CN101522672A - 杀虫的异噁唑啉类化合物 - Google Patents
杀虫的异噁唑啉类化合物 Download PDFInfo
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- CN101522672A CN101522672A CNA2007800381374A CN200780038137A CN101522672A CN 101522672 A CN101522672 A CN 101522672A CN A2007800381374 A CNA2007800381374 A CN A2007800381374A CN 200780038137 A CN200780038137 A CN 200780038137A CN 101522672 A CN101522672 A CN 101522672A
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- formula
- compound
- trifluoromethyl
- compounds
- halogen
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- 230000000749 insecticidal effect Effects 0.000 title description 14
- -1 cyano, nitro, amino Chemical group 0.000 claims abstract description 83
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
- 150000002367 halogens Chemical class 0.000 claims abstract description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 244000000054 animal parasite Species 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 4
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- 230000008018 melting Effects 0.000 description 14
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
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Abstract
新的式(I)异噁唑啉类化合物,其中A代表C或N;R代表卤代烷基;X代表卤素或卤代烷基;l代表0、1或2;Y代表卤素、烷基、烷氧基、卤代烷基、氰基、硝基、氨基、酰基氨基、烷氧基羰基氨基、卤代烷氧基羰基氨基或烷基磺酰基氨基;m代表0、1或2;并且G代表任意一种选自说明书中描述的杂环基;本发明还涉及该化合物用作杀虫剂以及在防治动物寄生虫中的用途。
Description
本发明涉及新的异噁唑啉类化合物、其制备方法、其作为杀虫剂的用途以及该异噁唑啉类化合物的新的中间体,以及它们在防治动物寄生虫中的用途。
WO 2005/085216描述了用异噁唑啉取代的苯甲酰胺可用作防治害虫的药剂。
现已发现下式(I)的新的异噁唑啉类化合物
其中:
A 代表C或N;
R 代表卤代烷基;
X 代表相同或不同的卤素或卤代烷基;
l 代表0、1或2;
Y 代表相同或不同的卤素、烷基、烷氧基、卤代烷基、氰基、硝基、氨基、酰基氨基、烷氧基羰基氨基、卤代烷氧基羰基氨基或烷基磺酰基氨基;
m 代表0、1或2;并且
G 代表任意一个选自式G-1至G-9表示的杂环基:
其中
Z 代表卤素、烷基、烷硫基、卤代烷基、氰基、硝基或氨基;并且
n 代表0或1。
本发明的式(I)化合物可通过如下方法获得,其中
(a)在惰性溶剂的存在下,以及如果合适在碱的存在下,将式(II)化合物与式(III)化合物反应,
其中A、Y、m和G具有与上文相同的含义,并且Hal代表卤素,
其中R、X和I具有与上文相同的含义,
或者
(b)在惰性溶剂的存在下,以及如果合适在碱的存在下,将式(IV)化合物与式(V)化合物反应,
其中A、R、X、l、Y、m和Hal具有如上文所述的含义,
G-H(V)
其中G具有如上文所述的含义,
或者
(c)如果G代表
则在惰性溶剂的存在下,将式(Ia)化合物与卤化剂反应,
其中A、R、X、l、Y和m具有上文所述的含义,
或者
(d)如果G代表
则在惰性溶剂的存在下,将式(VI)化合物与式(VII)化合物反应,
其中A、R、X、l、Y和m具有如上文所述的含义,
其中R1代表烷基,
或者
(e)如果G代表
则在碱的存在下将式(VI)化合物与1,2-二甲酰肼反应,
或者
(f)如果G代表
其中Rf代表全氟代烷基,
则在惰性溶剂的存在下,将式(VIII)化合物与叠氮化合物反应,
其中A、R、X、l、Y、m、Hal和Rf具有与上文相同的含义,
或者
(g)如果G代表
则在惰性溶剂的存在下,将式(VI)化合物与叠氮化合物和原甲酸三烷基酯反应,
或者
(h)如果其中A代表C,并且(Y)m中的至少一个代表3-NH2,则在惰性溶剂的存在下,使式(Ib)化合物还原,
其中R、X、l、Y、m和G具有如上文相同的含义,
或者
(i)如果其中“A”代表C,并且(Y)m中的至少一个代表3-NH-R2,其中R2代表酰基、烷氧基羰基、卤代烷氧基羰基或烷基磺酰基:
则在惰性溶剂的存在下,以及如果合适在碱的存在下,将式(Ic)化合物与式(IX)化合物反应,
其中R、X、l、Y、m和G具有与上文相同的含义,
R2-T (IX)
其中R2具有与上文相同的含义,且T代表卤素或羟基。
根据本发明,式(I)的异噁唑啉类化合物具有强杀虫活性。此外,已发现新的式(I)化合物具有显著的生物学特性,尤其适用于防治动物有害物,尤其是在农业、森林、贮存产品和材料的保护,以及兽医领域中出现的昆虫、蛛形纲动物和线虫。
本说明书中,术语“烷基”是指直链的或支链的C1-12烷基,如甲基、乙基、正丙基或异丙基、正丁基、异丁基、仲丁基或叔丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基或正十二烷基,优选为C1-6烷基,最优选C1-4烷基。烷基基团可以是未取代的,或者是被至少一个合适的取代基取代,所述合适的取代基选自本文中作为Y所提到的那些取代基。
“烷氧基”、“卤代烷基”、“烷氧基羰基氨基”、“卤代烷氧基羰基氨基”和“烷基磺酰基氨基”中各术语的烷基部分的实例为上文提及的“烷基”实例。
术语“酰基氨基”是指,例如烷基羰基氨基、环丙基羰基氨基和苯甲酰基,其中烷基部分的实例为上文提及的“烷基”。酰基氨基可以是未取代的,或者被至少一个合适的取代基取代,所述合适的取代基选自本文中作为Y所提到的取代基。
术语“卤素”是指氟、氯、溴或碘,优选氟、氯或溴。
“卤代烷基”和“卤代烷氧基羰基氨基”的卤素部分的实例为上文所述的“卤素”实例。
本发明的式(I)化合物中,优选的实例为这样的式(I)化合物,其中
A 代表C或N;
R 代表C1-4卤代烷基;
X 代表相同或不同的卤素或C1-4卤代烷基;
l 代表0、1或2;
Y 代表相同或不同的卤素、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、氰基、硝基、氨基、C1-4烷基-羰基氨基、环丙基羰基氨基、苯甲酰基氨基、C1-4烷氧基-羰基氨基、C1-4卤代烷氧基-羰基氨基或C1-4烷基-磺酰基氨基;
m 代表0、1或2;并且
G 代表任何一个选自下式G-1至G-9所示的杂环基:
其中
Z 代表卤素、甲基、甲硫基、三氟甲基、氰基、硝基或氨基,并且
n 代表0或1。
本发明的式(I)化合物中,优选的实例还有这样的式(I)化合物,其中
A 代表C;
R 代表任选取代的C1-12卤代烷基;
X 代表相同或不同的卤素或任选取代的C1-12卤代烷基;
l 代表0、1或2;
Y 代表相同或不同的卤素、任选取代的C1-12烷基、C1-12烷氧基、C1-12卤代烷基、氰基、硝基、氨基、C1-12烷基-羰基氨基、环丙基羰基氨基、苯甲酰基氨基、C1-12烷氧基-羰基氨基、C1-12卤代烷氧基-羰基氨基或C1-12烷基-磺酰基氨基;
m 代表0、1或2;并且
G 代表任何一个选自下式G-1至G-9所示的杂环基:
其中
Z 代表卤素、甲基、甲硫基、三氟甲基、氰基、硝基或氨基,并且
n 代表0或1。
此外,在本发明的式(I)化合物中,优选的实例还有这样的式(I)化合物,其中
A 代表N;
R 代表任选取代的C1-12卤代烷基;
X 代表相同或不同的卤素或任选取代的C1-12卤代烷基;
l 代表0、1或2;
Y 代表相同或不同的卤素、任选取代的C1-12烷基、C1-12烷氧基、C1-12卤代烷基、氰基、硝基、氨基、C1-12烷基-羰基氨基、环丙基羰基氨基、苯甲酰基氨基、C1-12烷氧基-羰基氨基、C1-12卤代烷氧基-羰基氨基或C1-12烷基-磺酰基氨基;
m 代表0、1或2;并且
G 代表任何一个选自下式G-1至G-9所示的杂环基:
其中
Z 代表卤素、甲基、甲硫基、三氟甲基、氰基、硝基或氨基,并且
n 代表0或1。
在本发明的式(I)化合物中,特别优选的实例为这样的式(I)化合物,其中:
A 代表C或N;
R 代表三氟甲基或五氟乙基;
X 代表相同或不同的氟、氯、溴或三氟甲基;
l 代表0、1或2;
Y 代表相同或不同的卤素、C1-2烷基、C1-2烷氧基、C1-2卤代烷基、氰基、硝基、氨基、C1-2烷基-羰基氨基、环丙基羰基氨基、苯甲酰基氨基、C1-2烷氧基-羰基氨基或C1-2烷基-磺酰基氨基;
m 代表0、1或2;并且
G 代表任何一个由下式G-1至G-9所示的杂环基:
其中
Z 代表卤素、甲基、甲硫基、三氟甲基、氰基、硝基或氨基;并且
n 代表0或1。
本发明的式(I)化合物含有不对称的碳,因此包括旋光异构体或几何异构体,或不同组成的相应的异构体混合物。本发明涉及纯的异构体和异构体混合物两者。
当使用例如3-氰基-N-羟基-4-(1H-1,2,4-三唑-1-基)苯甲亚氨酸酰氯和1,3-二氯-5-[1-(三氟甲基)乙烯基]苯作为原料时,上述制备方法(a)可由以下反应式表示。
当使用例如3-(4-氟-3-硝基苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑和1H-1,2,4-三唑作为原料时,上述制备方法(b)可由以下反应式表示。
当使用例如5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-吡唑-1-基)-苄腈作为原料、用N-氯代琥珀酰亚胺作卤化剂时,上文所述的制备方法(c)可由以下反应式表示。
当使用例如4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺和2,5-二甲氧基-四氢呋喃作为原料时,上文所述的制备方法(d)可由如下反应式表示。
当使用例如4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺和1,2-二甲酰基-肼作为原料时,上述制备方法(e)可由以下反应式表示。
当使用例如N-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-2,2,2-三氟乙亚氨酸酰氯和叠氮化钠作为原料时,上文所述的制备方法(f)可由以下反应式表示。
当使用例如4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺、原甲酸乙酯和叠氮化钠作为原料时,上文所述的制备方法(g)可由以下反应式表示。
当使用例如1-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-硝基苯基}-1H-1,2,4-三唑作为原料使其还原时,上文所述的制备方法(h)可由以下反应式表示。
当使用例如5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯胺和乙酰氯作为原料时,上文所述的制备方法(i)可由以下反应式表示。
制备方法(a)中使用的原料即式(II)化合物是新的化合物,其可通过将式(X)化合物与卤化试剂反应获得,
其中A、Y、m和G具有与上文相同的含义。
上述式(X)化合物可通过将式(XI)化合物与羟胺或其盐反应获得,
其中A、Y、m和G具有与上文相同的含义。
式(XI)化合物可通过将例如式(XII)化合物与式(V)化合物反应获得,
其中A、Y、m和Hal具有与上文相同的含义。
式(XII)化合物是已知的,其实例包括:
4-氟苯甲醛、3,4-二氟苯甲醛、2-氯-4-氟苯甲醛、3-氯-4-氟苯甲醛、3-溴-4-氟苯甲醛、4-氟-3-碘苯甲醛、4-氟-3-甲基苯甲醛、4-氟-3-三氟甲基苯甲醛、2-氟-5-甲酰基苄腈以及3-氯烟碱醛。
前述醛可根据例如Journal of Medicinal Chemistry,2003,vol.46,pp.4232-4235中描述的方法合成。
已知的式(XI)化合物的实例是已知的,包括:
4-(1H-吡唑-1-基)苯甲醛、4-(1H-咪唑-1-基)苯甲醛、4-(1H-1,2,3-三唑-1-基)苯甲醛以及4-(1H-1,2,5-三唑-1-基)苯甲醛,这些化合物在Journalof Medicinal Chemistry,1998,vol.41,pp.2390-2410中有所描述;6-(1H-咪唑-1-基)烟碱醛(描述于WO 88/00468A中)、3-氟-4-(1H-咪唑-1-基)苯甲醛和3-氯-4-(1H-咪唑-1-基)苯甲醛(均描述于WO 2005/115990A中);3-溴-4-(1H-吡咯-1-基)苯甲醛和3-溴-4-(1H-咪唑-1-基)苯甲醛,它们在WO 2005/016862A中有所描述;3-氟-4-(1H-吡唑-1-基)苯甲醛和3-氟-4-(1H-1,2,4-三唑-1-基)苯甲醛,它们在WO 2002/046204A中有所描述。
新的式(XI)化合物的优选实例包括:
5-甲酰基-2-(1H-1,2,4-三唑-1-基)苄腈、
5-甲酰基-2-(4-硝基-1H-吡唑-1-基)苄腈和
5-甲酰基-2-(1H-四唑-1-基)苄腈。
许多式(X)化合物是新的,现有技术中并无记载。下式(Xa)化合物也是如此,
其中A、Y和m具有与上文相同的含义,且G1具有与G相同的含义,前提是当A代表C且m代表0时,G1不代表1H-咪唑-1-基。N-[4-(1H-咪唑-1-基)-苯基]羟胺已在WO 95/29163A中有所描述。
式(X)化合物的典型实例包括:
3-溴-4-(4-硝基-1H-吡唑-1-基)苯甲醛肟、3-溴-4-(4-氰基-1H-吡唑-1-基)苯甲醛肟、5-[(肟基)甲基]-2-(4-硝基-1H-吡唑-1-基)苄腈、5-[(肟基)甲基]-2-(4-氰基-1H-吡唑-1-基)苄腈、4-(1H-1,2,4-三唑-1-基)苯甲醛肟、3-氯-4-(1H-1,2,4-三唑-1-基)苯甲醛肟、3-溴-4-(1H-1,2,4-三唑-1-基)苯甲醛肟、3-甲基-4-(1H-1,2,4-三唑-1-基)苯甲醛肟、4-(1H-1,2,4-三唑-1-基)-3-三氟甲基-苯甲醛肟、5-[(肟基)甲基]-2-(1H-1,2,4-三唑-1-基)-苄腈、6-(1H-1,2,4-三唑-1-基)烟碱醛肟和5-[(肟基)甲基]-2-(1H-四唑-1-基)-苄腈。
式(II)、(X)和(Xa)化合物包括旋光异构体或几何异构体或者不同组成的相应的异构体混合物。本发明涉及纯的异构体和异构体混合物两者。
另外,可用于制备式(II)化合物的卤化试剂通常是本领域技术人员已知的,包括例如,氯、溴、碘、N-氯琥珀酰亚胺、N-溴琥珀酰亚胺、N-碘琥珀酰亚胺、1,3-二氯-5,5-二甲基乙内酰脲、1,3-二溴-5,5-二甲基乙内酰脲、苄基三甲基四氯碘酸铵和次氯酸钠。
制备方法(a)的原料式(II)化合物的典型实例包括例如:
3-溴-N-羟基-4-(4-硝基-1H-吡唑-1-基)-苯甲酰亚胺氯、3-溴-N-羟基-4-(4-氰基-1H-吡唑-1-基-苯甲酰亚胺氯、3-氰基-N-羟基-4-(4-硝基-1H-吡唑-1-基)-苯甲酰亚胺氯、3-氰基-N-羟基-4-(4-氰基-1H-吡唑-1-基)-苯甲酰亚胺氯、N-羟基-4-(1H-1,2,4-三唑-1-基)-苯甲酰亚胺氯、3-氯-N-羟基-4-(1H-1,2,4-三唑-1-基-苯甲酰亚胺氯、3-溴-N-羟基-4-(1H-1,2,4-三唑-1-基)-苯甲酰亚胺氯、N-羟基-3-甲基-4-(1H-1,2,4-三唑-1-基)-苯甲酰亚胺氯、N-羟基-4-(1H-1,2,4-三唑-1-基)-3-三氟甲基苯甲酰亚胺氯、3-氰基-N-羟基-4-(1H-1,2,4-三唑-1-基)-苯甲酰亚胺氯、N-羟基-6-(1H-1,2,4-三唑-1-基)吡啶-3-酰亚胺氯和3-氰基-N-羟基-4-(1H-四唑-1-基)-苯甲酰亚胺氯。
用作制备方法(a)中其它原料的式(III)化合物包括已知的化合物,它们例如描述于Journal of Organic Chemistry,1991,vol.56,pp.7336-7340、ditto 1994,vol.59,pp.2898-2901和ditto,1999,vol.95,pp.167-170,以及WO 2005/05085216A中。
另外,式(III)化合物可通过这些出版物中的方法合成。
式(III)化合物的典型实例包括:
[1-(三氟甲基)乙烯基]苯、1,3-二氟-5-[1-(三氟甲基)乙烯基]苯、1-氯-3-[1-(三氟甲基)乙烯基]苯、1,3-二氯-5-[1-(三氟甲基)乙烯基]苯、1-三氟甲基-3-[1-(三氟甲基)乙烯基]-苯、1-三氟甲基-4-[1-(三氟甲基)乙烯基]-苯和1,3-二(三氟甲基)-5-[1-(三氟甲基)-乙烯基]苯。
制备方法(a)可根据WO 2004/018410A、WO 2005/085216A或Tetrahedron,2000,vol.56,pp.1057-1064中描述的方法实施。
制备方法(a)的反应可在合适的稀释剂或溶剂中实施。稀释剂或溶剂的实例包括脂族烃(己烷、环己烷、庚烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醇(甲醇、乙醇、异丙醇等)、醚(二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等)、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)、水或这些溶剂的混合物。
制备方法(a)的反应可在使用一种碱的情况下实施,例如一种碱金属碱,如碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、醋酸钠、醋酸钾、甲醇钠、乙醇钠或叔丁醇钾;或者一种有机碱,如三乙胺、二异丙基乙基胺、三丁胺、N-甲基吗啉、N,N-二甲基苯胺、N,N-二乙基苯胺、4-叔丁基-N,N-二甲基苯胺、吡啶、甲基吡啶、二甲基吡啶、二氮杂双环十一烯、二氮杂双环辛烷或咪唑。
制备方法(a)的反应可在宽的温度范围内实施。该反应可在通常约-78至约200℃的温度范围内进行,优选在-10至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
当实施制备方法(a)时,例如对应于每摩尔式(II)化合物,将1至2摩尔的式(III)化合物与1摩尔至稍过量的一种碱在稀释剂如DMF中反应,生成式(I)的目的化合物。
制备方法(b)中的原料式(IV)化合物是已知的,例如描述于WO2005/085216A中。
式(IV)化合物的典型实例包括:
5-(3,5-二氯苯基)-3-(4-氟苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(4-氟苯基)-5-[3-(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑、5-[3,5-二(三氟甲基)苯基]-3-(4-氟-苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(3-氯-4-氟苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(3-氯-4-氟苯基)-5-[3-(三氟甲基)-苯基]-5-(三氟甲基)-4,5-二氢异噁唑、5-[3,5-二(三氟甲基)苯基]-3-(3-氯-4-氟苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(3-溴-4-氟苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(3-溴-4-氟苯基)-5-[3-(三氟甲基)-苯基]-5-(三氟甲基)-4,5-二氢异噁唑、5-[3,5-二(三氟甲基)苯基]-3-(3-溴-4-氟苯基)-5-(三氟甲基)-4,5-二氢异噁唑、5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-氟苄腈、2-氟-5-{5-(三氟甲基)-5-[3-(三氟甲基)苯基]-4,5-二氢异噁唑-3-基}-苄腈、5-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}-2-氟苄腈、3-(4-氟-3-硝基苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(4-氯-3-硝基苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑、3-(4-氟-3-硝基苯基)-5-[3-(三氟甲基)-苯基-5-(三氟甲基)-4,5-二氢异噁唑、5-[3,5-二(三氟甲基)苯基]-3-(4-氟-3-硝基苯基)-5-(三氟甲基)-4,5-二氢异噁唑和3-(6-氯吡啶-3-基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑。
制备方法(b)的原料式(V)化合物是有机化学领域中已知的,其典型实例包括:
1H-咪唑、1H-吡唑、4-甲基-1H-吡唑、4-氟-1H-吡唑、4-氯-1H-吡唑、4-溴-1H-吡唑、4-碘-1H-吡唑、4-硝基-1H-吡唑、4-甲基-1H-吡唑、3-三氟甲基-1H-吡唑、4-三氟甲基-1H-吡唑、4-氰基-1H-吡唑、1H-1,2,3-三唑,1H-1,2,4-三唑,1H-四唑,5-甲基-1H-四唑和5-(甲基硫)-1H-四唑。
这些唑类化合物可通过Journal of Medicinal Chemistry,2005,vol.48,pp.5780-5793、Monatshefte für Chemie,1993,vol.124,pp.199-207和Tetrahedron Letters,1996,vol.37,pp.1829-1832中描述的方法制备。
制备方法(b)的反应可在合适的稀释剂或溶剂中实施。所述稀释剂或溶剂的实例包括:
脂族烃(己烷、环己烷、庚烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚(二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等)、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)、水或这些溶剂的混合物。
制备方法(b)的反应可使用一种碱实施,例如一种碱金属碱,如氢化锂、氢化钠、氢化钾、氨基锂、氨基钠、二异丙基氨基锂、丁基锂、叔丁基锂、三甲基甲硅烷基锂、六甲基二硅烷重氮锂、碳酸钠、碳酸钾、醋酸钠、醋酸钾、甲醇钠、乙醇钠或叔丁醇钾;或者一种有机碱,如三乙胺、二异丙基乙胺、三丁胺、N-甲基吗啉、N,N-二甲基苯胺、N,N-二乙基苯胺、4-叔丁基-N,N-二甲基苯胺、吡啶、甲基吡啶、二甲基吡啶、二氮杂双环十一烯、二氮杂双环辛烷或咪唑。
制备方法(b)的反应可在宽的温度范围内实施。该反应可在通常约-78至约200℃的温度范围内进行,优选在-10至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
当实施制备方法(b)时,例如对应于每摩尔式(IV)化合物,将1至3摩尔的式(V)化合物在1摩尔至3摩尔碱的存在下,在稀释剂如DMF中反应,生成式(I)的目的化合物。
制备方法(c)中用作原料的式(Ia)化合物与一部分式(I)化合物对应。
卤化试剂的实例包括上文示例出的同类化合物。
制备方法(c)的反应可在合适的稀释剂或溶剂中实施。所述稀释剂或溶剂的实例包括:
脂族烃(己烷、环己烷、庚烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚(二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等)、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)或这些溶剂的混合物。
制备方法(c)的反应可使用一种卤化试剂实施,所述卤化试剂例如氯、溴、碘、N-氯琥珀酰亚胺、N-溴琥珀酰亚胺、N-碘琥珀酰亚胺、1,3-二氯-5,5-二甲基乙内酰脲、1,3-二溴-5,5-二甲基乙内酰脲或次氯酸钠。
制备方法(c)的反应可在宽的温度范围内实施。该反应可在通常约-78至约200℃的温度范围内进行,优选在-10至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选0.1至24小时。
当实施制备方法(c)时,例如,对应于每摩尔式(Ia)化合物,有1摩尔至稍过量的N-氯琥珀酰亚胺在稀释剂如DMF中反应,生成式(I)的目的化合物。
制备方法(d)的原料式(VI)化合物是已知的,并在例如WO2005/085216A中有所描述,其典型实例包括:
4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺、2-氯-4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺、2-溴-4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺、4-{5-[3-(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺、2-氯-4-{5-[3-(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺、2-溴-4-{5-[3-(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺、4-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺、2-氯-4-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺和2-溴-4-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}苯胺。
制备方法(d)的原料式(VII)化合物是已知的,其典型实例包括:
2,5-二甲氧基四氢呋喃和2,5-二乙氧基四氢呋喃。
制备方法(d)的反应可在合适的稀释剂或溶剂中实施,该稀释剂或溶剂的实例包括:
脂族烃(己烷、环己烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚(二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等)、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、酸(乙酸等)、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)或这些溶剂的混合物。
制备方法(d)可在宽的温度范围内实施。该反应可在通常约0至约200℃的温度范围内进行,优选在室温至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
当实施制备方法(d)时,例如,对应于每摩尔式(VI)化合物,将1摩尔至5摩尔的2,5-二烷氧基四氢呋喃在稀释剂如乙酸中反应,生成式(I)的目的化合物。
制备方法(e)的原料式(VI)化合物与上述制备方法(d)中描述的相同。
另外,原料1,2-二甲酰基肼也是一种已知的化合物。
实施制备方法(e)时,在一种碱和三烷基卤代甲硅烷的存在下,将式(VI)化合物与1,2-二甲酰基肼反应,由此可得到对应的式(I)化合物。
三烷基卤代甲硅烷的具体实例可包括:三甲基氯甲硅烷、三乙基氯甲硅烷和三甲基溴甲硅烷。
制备方法(e)可根据Journal of Organic Chemistry,2001,vol.44,pp.3157-3165中描述的方法实施。
制备方法(e)的反应可使用一种碱实施,例如一种有机碱,如三乙胺、二异丙基乙胺、三丁胺、N-甲基吗啉、N,N-二甲基苯胺、N,N-二乙基苯胺、4-叔丁基-N,N-二甲基苯胺、吡啶、甲基吡啶、二甲基吡啶、二氮杂双环十一烯、二氮杂双环辛烷或咪唑。
制备方法(e)的反应可在宽的温度范围内实施。该反应可在通常约0至约200℃的温度范围内进行,优选在0至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
实施制备方法(e)时,例如对应于每摩尔式(VI)化合物,将1至5摩尔的1,2-二甲酰基肼、1至10摩尔的碱和1至25摩尔的三烷基卤代甲硅烷在大量过量的吡啶中反应,生成式(I)目的化合物。
制备方法(f)的原料式(VIII)化合物是新化合物,可通过将式(XIII)化合物与四卤化碳和式(XIV)的三价磷化合物反应而获得,
其中A、R、X、l、Y、m和Rf具有与上文所述相同的含义,
PL3 (XIV)
其中L代表C4-8烷基或芳基。
式(XIII)化合物也是新化合物,可通过将式(VI)化合物与全氟代烷基酰卤或全氟代烷基羧酸酐在碱的存在下反应。
上述四卤化碳是已知化合物。四卤化碳的具体实例包括四氯化碳和四溴化碳。式(XIV)的磷化合物是已知的,其具体实例包括:三丁基膦和三苯基膦。
上述全氟代烷基酰卤或全氟代烷基羧酸酐是已知化合物。
这些化合物的实例包括三氟乙酸酐、五氟丙酸酐和七氟丁酸酐。
制备方法(f)中使用的叠氮类化合物的具体实例包括叠氮化锂和叠氮化钠。
制备方法(f)可根据公开号为2005-154420A的日本专利申请(KOKAI)中描述的方法实施。
制备方法(f)的反应可在合适的稀释剂或溶剂中实施,其包括:
脂族烃(己烷、环己烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚[二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等]、胺(吡啶、三甲基吡啶)、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)或这些溶剂的混合物。
制备方法(f)可在宽的温度范围内实施。该反应可在通常约-78至约200℃的温度范围内进行,优选在室温即20℃至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
实施制备方法(f)时,例如,对应于每摩尔式(VIII)化合物,将1摩尔至2摩尔的叠氮化合物在稀释剂如乙腈中反应,生成式(I)的目的化合物。
制备方法(g)中的原料式(VI)化合物与在制备方法(d)中示例的该原料化合物相同。另外,叠氮化合物与在上述制备方法(f)中提及的该化合物相同。
此外,原甲酸三烷基酯是已知化合物,其具体实例可包括:原甲酸三甲酯和原甲酸三乙酯。
制备方法(g)的反应在在合适的稀释剂或溶剂中实施,其实例包括:
脂族烃(己烷、环己烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚[二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等]、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、酸(乙酸、丙酸等)、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)或这些溶剂的混合物。
制备方法(g)可在宽的温度范围内实施。该反应可在通常约0至约200℃的温度范围内进行,优选在室温即20℃至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选1至24小时。
实施制备方法(g)时,例如,对应于每摩尔式(VI)化合物,将1至3摩尔叠氮化合物与1至10摩尔原甲酸三烷基酯在稀释剂如乙酸中反应,生成式(I)目的化合物。
制备方法(g)可根据Journal of Medicinal Chemistry,2000,vol.43,pp.953-970中描述的方法实施。
式(Ib)化合物作为式(I)化合物的一部分被包括在本发明中。
制备方法(h)中的还原方法的实例包括使用锌、铁或氯化亚锡进行的反应;以及使用催化剂例如钯催化剂、镍催化剂、钴催化剂、铑催化剂、钌催化剂或铂催化剂进行的氢化反应。
制备方法(h)可在合适的稀释剂或溶剂中实施,其实例包括:
脂族烃(己烷、环己烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚[二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等]、酸(乙酸、丙酸等)、酯(乙酸乙酯、丙酸乙酯等)、水或这些溶剂的混合物。
制备方法(h)可在宽的温度范围内实施。该反应可在通常约0至约200℃的温度范围内进行,优选在室温即20℃至约150℃内进行。另外,尽管优选在常压下实施该反应,但该反应也可在升压或减压下进行。反应时间为0.1至72小时,优选0.5至24小时。
实施制备方法(h)时,例如,对应于每摩尔式(Ib)化合物,将3至5摩尔氯化亚锡和催化量的浓盐酸加入稀释剂如乙醇中,产生式(I)目的化合物。
式(Ic)化合物作为式(I)化合物的一部分被包括在本发明中。
另外,式(IX)化合物是已知化合物,其典型实例包括:
乙酰氯、丙酰氯、异丁酰氯、环丙烷甲酰氯、苯甲酰氯、氯甲酸甲酯、氯甲酸乙酯、甲磺酰氯和苯甲酸。
制备方法(i)的反应可在合适的稀释剂或溶剂中实施,其实例包括:
脂族烃(己烷、环己烷等)、芳香烃(苯、甲苯、二甲苯、氯苯等)、醚[二乙醚、二丁基醚、二甲氧基乙烷(DME)、四氢呋喃、二噁烷等]、酰胺[二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮等]、腈(乙腈、丙腈等)、二甲基亚砜(DMSO)、水或这些溶剂的混合物。
制备方法(i)的反应可使用一种碱实施,例如一种碱金属碱,如氢化锂、氢化钠、氢化钾、氨基锂、氨基钠、二异丙基氨基锂、丁基锂、叔丁基锂、三甲基甲硅烷基锂、六甲基二硅烷重氮锂、碳酸钠、碳酸钾、醋酸钠、醋酸钾、甲醇钠、乙醇钠或叔丁醇钾;或者一种有机碱,如三乙胺、二异丙基乙胺、三丁胺、N-甲基吗啉、N,N-二甲基苯胺、N,N-二乙基苯胺、4-叔丁基-N,N-二甲基苯胺、吡啶、甲基吡啶、二甲基吡啶、二氮杂双环十一烯、二氮杂双环辛烷或咪唑。
制备方法(i)的反应可使用一种缩合剂实施,例如,1,3-二环己基碳二亚胺或1-乙基-3-(3’-二甲基氨基-丙基)碳二亚胺或其盐。
实施制备方法(i)时,例如,对应于每摩尔式(Ic)化合物,使1至2摩尔式(IX)化合物在1至2摩尔碱存在下在稀释剂如THF中反应,生成式(I)的目的化合物。
用于制备式(I)化合物的式(II)、(Xa)、(VIII)和(XIII)是新化合物。
式(VIII)和(XIII)可一起由下式(XV)表示:
其中A、R、X、l、Y和m具有如上文所述的相同含义,并且M代表由下式表示的基团:
其中Rf和Hal具有本文所述的相同含义。
根据本发明,式(I)化合物具有强杀虫活性。此外,本发明的化合物显示出针对动物有害物的强活性,因此可用于防治动物有害物。
因此,本发明的式(I)所表示的化合物可用作杀虫剂,或用于制备防治动物有害物的组合物。
本发明中,所有对害虫具有杀虫活性的化合物、组合物以及材料在本文中都被称为杀虫剂。
此外,由本发明的式(I)所示的活性化合物显示出特异的防治有害昆虫的效果,而不会对栽培植物具有任何植物毒性。
因此,本发明的化合物可被用于防治多种不同的动物有害物。尤其是防治刺吸口器昆虫、嘴嚼口器昆虫和其它植物寄生的害虫,贮存产品害虫和卫生害虫。此外,本发明的化合物还可被用于对付例如根除和消灭这些害虫。
这些害虫的实例包括:
昆虫纲(Insecta),鞘翅目(Coleoptera)害虫,例如绿豆象(Callosobruchus Chinensis)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium castaneum)、马铃薯瓢虫(Epilachna vigintioctomaculata)、细胸金针虫(Agriotes fuscicollis)、红铜丽金龟(Anomala rufocuprea)、马铃薯甲虫(Leptinotarsa decemlineata)、叶甲属(Diabrotica spp.)、松墨天牛(Monochamus alternatus)、稻水象甲(Lissorhoptrusoryzophilus)、褐粉蠹(Lyctus bruneus)和黄守瓜(Aulacophorafemoralis);
鳞翅目(Lepidoptera)害虫,例如,舞毒蛾(Lymantria dispar)、天幕毛虫(Malacosoma neustria)、纹白蝶(Pieris rapae)、斜纹夜蛾(Spodoptera litura)、甘蓝灯蛾(Mamestra brassicae)、二化螟(Chilosuppressalis)、玉米螟(Pyrausta nubilalis)、粉斑螟(Ephestia cautella)、苹卷蛾(Adoxophyes orana)、苹果蠹蛾(Carpocapsa pomonella)、Agrotisfucosa、大蜡螟(Galleria mellonella)、小菜蛾(Plutellamaculipennis)、烟芽夜蛾(Heliothis virescens)和柑桔潜叶蛾(Phyllocnistis citrella);
半翅目(Hemiptera)害虫,例如黑尾叶蝉(Nephotettix cincticeps)、褐飞虱(Nilaparvata lugens)、康氏粉蚧(Pseudococcus comstocki)、矢尖盾蚧(Unaspis yanonensis)、桃蚜(Myzus persicas)、苹蚜(Aphis pomi)、棉蚜(Aphis gossypii)、Phopalosiphum pseudobrassicas、梨冠网蝽(Stephanitis nashi)、Nazara spp、温室白粉虱(Trialeurodesvaporariorm)和Pshylla spp;
缨翅目(Thysanoptera)害虫,例如棕榈蓟马(Thrips palmi)和Franklinella occidental;
直翅目(Orthoptera)害虫,例如德国蠊(Blattella germanica)、美洲大蠊(Periplaneta americana)、非洲蝼蛄(Gryllotalpa africana)、和东亚飞蝗(Locusta migratoria migratoriaodes);
等翅目(Isoptera)害虫,例如黄胸散白蚁(Reticulitermes speratus)和台湾乳白蚁(Coptotermes formosanus);以及
双翅目(Diptera)害虫,例如家蝇(Musca domestica)、埃及伊蚊(Aedes aegypti)、玉米种蝇(Hylemia platura)、尖音库蚊(Culex pipiens)、中华按蚊(Anopheles slnensis)、三带喙库蚊(Culex tritaeniorhychus)和三叶斑潜蝇(Liriomyza trifolii);
以及蜱螨目(Acarina),例如朱砂叶螨(Tetranychus cinnabarinus)、二斑叶螨(Tetranychus urticae)、桔全爪螨(Panonychus citri)、刺皮瘿螨(Aculops pelekassi)和跗线螨属(Tarsonemus spp.)。
害虫的其它实例包括:
线虫纲(Nematoda),例如南方根结线虫(Meloidogyne incognita)、松材线虫(Bursaphelenchus lignicolus Mamiya et Kiyohara)、水稻干尖线虫(Aphelenchoides besseyi)、大豆抗胞囊线虫(Heterodera glycines)和短体线虫属(Pratylenchus spp.)。
此外,已发现本发明的新化合物对动物寄生虫具有活性,因此可有效地用于对付多种有害的动物寄生虫(体内寄生虫和体外寄生虫),例如兽医领域的昆虫和蠕虫。
这些动物寄生虫的实例可包括以下害虫:
昆虫,例如胃蝇属(Gastrophilus spp.)、螫蝇属(Stomoxys spp.)、嚼虱属(Trichodectes spp.)、红猎蝽属(Rhodnius spp.)、犬栉首蚤(Ctenocephalides canis)、温带臭虫(Cimx lecturius)、猫栉首蚤(Ctenocephalides felis)和铜绿蝇(Lucila cuprina)。
蜱螨目,例如,钝缘蜱属(Ornithodoros spp.)、硬蜱属(Ixodes spp.)和牛蜱属(Boophilus spp.)。
如前所述,在兽医领域即在兽药领域中,本发明的活性化合物对动物寄生虫(体外寄生虫和体内寄生虫),例如硬蜱、软蜱、马痒螨、恙螨、蝇(叮咬和吸食)、寄生蝇幼虫、虱、毛虱、羽螨、羽虱和蚤也具有活性。
所述寄生虫包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phtirus spp.、管虱属(Solenopotes spp.);具体实例为:棘颚虱(Linognathus setosus)、狐颚虱(Linognathus vituli)、绵羊颚虱(Linognathus ovillus)、Linognathusoviformis、足颚虱(Linognathus pedalis)、狭颚虱(Linognathusstenopsis)、Haematopinus asini macrocephalus、阔胸血虱(Haematopinuseurysternus)、猪血虱(Haematopinus suis)、头虱(Pediculus humanuscapitis)、体虱(Pediculus humanus corporis)、Phylloera vastatrix、阴虱(Phthirus pubis)、牛管虱(Solenopotes capillatus);
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menoponspp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属、猫羽虱属(Felicola spp.);具体实例为:牛毛虱(Bovicola bovis)、绵羊虱(Bovicolaovis)、Bovicola limbata、牛畜虱(Damalina bovis)、犬虱(Trichodectescanis)、猫羽虱(Felicola subrostratus)、山羊毛虱(Bovicola caprae)、Lepikentron ovis、Werneckiella equi;
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culexspp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoidesspp.)、斑虻属(Chrysops spp.)、Odagmia spp.、Wilhelmia spp.、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphora spp.)、绿蝇属(Luciliaspp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)、鼻狂蝇属(Rhinoestrus spp.)、大蚊属(Tipula spp.);具体实例为:埃及伊蚊、白纹伊蚊(Aedes albopictus)、带喙伊蚊(Aedes taeniorhynchus)、刚比亚按蚊(Anopheles gambiae)、五斑按蚊(Anopheles maculipennis)、红头丽蝇(Calliphora erythrocephala)、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culex quinquefasciatus)、尖音库蚊、环喙库蚊(Culextarsalis)、夏厕蝇(Fannia canicularis)、肉蝇(Sarcophaga carnaria)、厩螫蝇(Stomoxys calcitrans)、沼泽大蚊(Tipula paludosa)、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、轮丝蚋(Simuliumreptans)、Phlebotomus papatasi、长管白蛉(Phlebotomus longipalpis)、Odagmia ornata、Wilhelmia equina、Boophthora erythrocephala、多声虻(Tabanus bromius)、Tabanus spodopterus、Tabanus atratus、Tabanussudeticus、古氏瘤虻(Hybomitra ciurea)、盲斑虻(Chrysops caecutiens)、弧斑虻(Chrysops relictus)、高额麻虻(Haematopota pluvialis)、Haematopota italica、秋家蝇(Musca autumnalis)、家蝇、西方角蝇(Haematobia irritans irritans)、东方角蝇(Haematobia irritans exigua)、刺扰血蝇(Haematobia stimulans)、Hydrotaea irritans、白斑齿股蝇(Hydrotaea albipuncta)、白头裸金蝇(Chrysomya chloropyga)、蛆症金蝇(Chrysomya bezziana)、羊狂蝇(Oestrus ovis)、牛皮蝇(Hypodermabovis)、纹皮蝇(Hypoderma lineatum)、Przhevalskiana silenus、人肤蝇(Dermatobia hominis)、绵羊虱蝇(Melophagus ovinus)、Lipoptenacapreoli、Lipoptena cervi、多异长足瓢虫(Hippobosca variegata)、马虱蝇(Hippobosca equina)、肠胃蝇(Gasterophilus intestinalis)、赤尾胃蝇(Gasterophilus haemorroidalis)、裸节胃蝇(Gasterophilus inermis)、鼻胃蝇(Gasterophilus nasalis)、黑角胃蝇(Gasterophilus nigricornis)、黑腹胃蝇(Gasterophilus pecorum)、蜂虱蝇(Braula coeca);
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉首蚤属(Ctenocephalides spp.)、Tunga spp.、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllus spp.);具体实例为:犬栉首蚤、猫栉首蚤、人蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤(Xenopsyllacheopis);
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatoma spp.)、红猎蝽属、锥蝽属(Panstrongylus spp.);
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊、德国蠊、夏柏拉蟑螂属(Supella spp.)(例如棕带蜚蠊(Suppellalongipalpa);
蜱螨亚纲(Acari或Acarina)及后气门目(Metastigmate)和中气门目(Mesostigmata),例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属、花蜱属(Amblyomma spp.)、牛蜱属(Rhipicephalus(Boophilus)spp)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalommaspp.)、皮刺螨属(Dermanyssus spp.)、扇头蜱属(Rhipicephalus spp.)(多宿主蚤的原先的属)Ornithonyssus spp.、肺刺螨属(Pneumonyssusspp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)、蜂盾螨属(Acarapis spp.);其具体实例为:波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argas reflexus)、非洲钝缘蜱(Ornithodorus moubata)、Otobiusmegnini、微小牛蜱(Rhipicephalus(Boophilus)microplus)、Rhipicephalus(Boophilus)decoloratus、具环牛蜱(Rhipicephalus(Boophilus)annulatus)、Rhipicephalus(Boophilus)calceratus、小亚璃眼蜱(Hyalomma anatolicum)、埃及璃眼蜱(Hyalomma aegypticum)、边缘璃眼蜱(Hyalomma marginatum)、Hyalomma transiens、Rhipicephalusevertsi、蓖子硬蜱(Ixodes ricinus)、六角硬蜱(Ixodes hexagonus)、原野硬蜱(Ixodes canisuga)、Ixodes pilosus、Ixodes rubicundus、肩突硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、嗜群血蜱(Haemaphysalis concinna)、刻点血蜱(Haemaphysalis punctata)、Haemaphysalis cinnabarina、Haemaphysalis otophila、Haemaphysalisleachi、长角血蜱(Haemaphysalis longicorni)、边缘革蜱(Dermacentormarginatus)、网纹革蜱(Dermacentor reticulatus)、Dermacentor pictus、白纹革蜱(Dermacentor albipictus)、安氏革蜱(Dermacentor andersoni)、变异革蜱(Dermacentor variabilis)、边缘璃眼蜱(Hyalommamauritanicum)、血红扇头蜱(Rhipicephalus sanguineus)、囊形扇头蜱(Rhipicephalus bursa)、非洲扇头蜱(Rhipicephalusappendiculatus)、Rhipicephalus capensis、图兰扇头蜱(Rhipicephalusturanicus)、Rhipicephalus zambeziensis、美洲花蜱(Amblyommaamericanum)、彩饰花蜱(Amblyomma variegatum)、有斑花蜱(Amblyomma maculatum)、淫性钝眼蜱(Amblyomma hebraeum)卡延钝眼蜱(Amblyomma cajennense)、鸡皮刺螨(Dermanyssusgallinae)、囊禽刺螨(Ornithonyssus bursa)、林禽刺螨(Ornithonyssussylviarum)、大蜂螨(Varroa jacobsoni);
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodexspp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarusspp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、耳疥螨属(Otodectesspp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.);其具体实例为:雅氏姬螯螨(Cheyletiellayasguri)、Cheyletiella blakei、犬蠕形螨(Demodex canis)、牛蠕形螨(Demodex bovis)、绵羊蠕形螨(Demodex ovis)、山羊蠕形螨(Demodexcaprae)、马蠕形螨(Demodex equi)、Demodex caballi、猪蠕形螨(Demodex suis)、秋收恙螨(Neotrombicula autumnalis)、Neotrombicula desaleri、 xerothermobia、红恙螨(Trombicula akamushi)、耳痒螨(Otodectes cynotis)、猫背肛螨(Notoedres cati)、犬疥螨(Sarcoptis canis)、牛疥螨(Sarcoptes bovis)、绵羊疥螨(Sarcoptes ovis)、山羊疥螨(Sarcoptes rupicaprae(=S.caprae))、马疥螨(Sarcoptes equi)、猪疥螨(Sarcoptes suis)、绵羊瘙螨(Psoroptes ovis)、兔瘙螨(Psoroptes cuniculi)、马瘙螨(Psoroptesequi)、牛痒螨(Chorioptes bovis)、绵羊痒螨(Psoergates ovis)、Pneumonyssoidic Mange、狗鼻肺刺螨(Pneumonyssoides caninum)、伍氏蜂跗线螨(Acarapis woodi)。
本发明的式(I)活性化合物也适用于防治侵袭以下动物的节肢动物:农业家畜,例如黄牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、家鸡、火鸡、鸭、鹅、蜜蜂,其它玩赏动物,例如狗、猫、笼鸟、观赏鱼,以及所谓的试验动物,例如仓鼠、豚鼠、大鼠和小鼠。
通过防治所述节肢动物,旨在减少死亡和改善(肉、奶、毛、皮、蛋、蜜等的)品质,从而可通过使用本发明的活性化合物使畜牧更经济、更简便。
本发明的活性化合物以已知方式通过以下方式用于兽医领域和畜牧中:通过例如片剂、胶囊剂、口服饮剂、兽用顿服药、颗粒剂、膏剂、丸剂、喂服(feed-through)法、栓剂的方式进行肠内给药,可通过例如注射(肌内、皮下、静脉、腹膜内等)、植入进行肠外给药,可鼻部给药,可通过例如沐浴或浸泡、喷雾、泼浇和点滴、清洗、撒粉的形式进行皮肤给药,以及借助于包含活性化合物的模型制品、例如项圈、耳标、尾标、肢体缚带(limb band)、笼头、标识器等。还可将活性化合物制成香波或者可用在气雾剂、无压喷雾剂如泵压喷雾剂和雾化喷雾剂中的合适制剂。
用于家畜、家禽、玩赏动物等时,式(I)的活性化合物可作为包含1至80重量%活性化合物的制剂(例如粉剂、可湿性粉剂[“WP”]、乳剂、乳油[“EC”]、可流动制剂、均匀的溶剂和悬浮剂[“SC”])直接使用或稀释(如100至10000倍)后使用,或可以化学药浴剂(chemicalbath)形式使用。
此外,已发现本发明的活性化合物还对毁坏工业材料的昆虫具有有效的杀虫作用。
以实例并且优选但不受任何限制的方式可提出以下昆虫:
甲虫,例如
北美家天牛(Hylotrupes bajulus)、Chlorophorus pilosis、家具窃蠹(Anobium punctatum)、报死窃蠹(Xestobium rufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobium pertinex、松窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、褐异翅长蠹(Heterobostrychus brunneus)、棘长蠹种(Sinoxylonspec.)、竹长蠹(Dinoderus minutus)。
革翅目(Heminoptera),例如
大树蜂(Sirex juvencus)、枞大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)、Urocerus augur。
白蚁,例如
欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermesbrevis)、灰点异白蚁(Heterotermes indicola)、欧美散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、南欧网纹白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermesdarwiniensis)、内华达古白蚁(Zootermopsis nevadensis)、家白蚁(Coptotermes formosanus)。
蠹虫(Bristletail),例如衣鱼(Lepisma saccharina)。
本发明中工业材料的含义应理解为非活体材料,例如,优选为聚合物、粘合剂、胶料、纸张和板材、皮革、木材和木材制品和涂料。
如果合适,用于保护工业材料并含有至少一种本发明化合物的即用的组合物还可额外地包括其他活性成分,例如至少一种杀虫剂和/或至少一种杀菌剂。合适的杀虫剂和/或杀菌剂优选为本发明中提及的杀虫剂和/或杀菌剂。
本发明的化合物还可用于保护物体上的生长物,尤其是与咸水或微咸水接触的船体、筛、网、建筑物、系泊设备及信号系统。
此外,本发明的化合物可单独使用或与其它活性成分结合用作防污剂。
在卫生领域中,已发现本发明的活性化合物亦适于防治动物有害物,特别是用于保护住宅楼宇内卫生领域和贮存产品。已发现它们尤其对封闭空间内的昆虫、蛛形纲动物和螨虫具有活性,所述封闭空间例如住所、工厂车间、办公室、交通工具舱室等。为防治这些害虫,它们可单独或与其他活性成分和助剂结合用于住宅楼宇的杀虫产品中。它们对敏感和抗性物种以及全部发育阶段均具有活性。
所述动物有害物包括:
蝎目(Scorpionidea),例如地中海黄蝎(Buthus occitanus);
蜱螨目(Acarina),例如波斯锐缘蜱、鸽锐缘蜱、苔螨亚种(Bryobiassp.)、鸡皮刺螨、家嗜甜螨(Glyciphagus domesticus)、非洲钝缘蜱(Ornithodorus moubat)、血红扇头蜱、阿氏真恙螨(Trombiculaalfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoides pteronissimus)、法嗜皮螨(Dermatophagoidesforinae);
蜘蛛目(Araneae),例如捕鸟蛛(Aviculariidae)、圆蛛(Araneidae);
盲蛛目(Opiliones),例如螯蝎(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、长踦盲蛛(Opiliones phalangium);
等足目(Isopoda),例如栉水虱(Oniscus asellus)、球鼠妇(Porcellioscaber);
倍足目(Diplopoda),例如Blaniulus guttulatus、山蛩虫(Polydesmus spp.)
唇足目(Chilopoda),例如地蜈蚣(Geophilus spp.);
衣鱼目(Zygentoma),例如栉衣鱼属(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismodes inquilinus);
蜚蠊目(Blattaria),例如东方蜚蠊、德国蠊、亚洲蠊(Blattellaasahinai)、马德拉蜚蠊(Leucophaea maderae)、角腹蠊属(Panchloraspp.)、木蠊属(Parcoblatta spp.)、澳洲大蠊(Periplaneta australasiae)、美洲大蠊、大褐大蠊(Periplaneta brunnea)、烟色大蠊(Periplanetafuliginosa)、棕带蜚蠊(Supella longipalpa);
跳跃亚目(Saltatoria),例如家蟋(Acheta domesticus);
革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia);
等翅目,例如木白蚁属(Kalotermes spp.)、散白蚁属(Reticulitermes spp);
啮虫目(Psocoptera),例如Lepinatus spp.、粉啮虫属(Liposcelisspp.);
鞘翅目,例如圆皮蠹属(Anthrenus spp.)、毛皮蠹属(Attagenusspp.)、皮蠹属(Dermestes spp.)、长头谷盗(Latheticus oryzae)、隐跗郭公虫属(Necrobia spp.)、蛛甲属(Ptinus spp.)、谷蠹(Rhizopertha dominica)、谷象(Sitophilus granarius)、米象(Sitophilus oryzae)、玉米象、药材甲(Stegobium paniceum);
双翅目,例如埃及伊蚊、白纹伊蚊、带喙伊蚊、按蚊属、红头丽蝇、高额麻虻、五带淡色库蚊、尖音库蚊、环喙库蚊、果蝇属(Drosophilaspp.)、夏厕蝇、家蝇、白蛉属、肉蝇、蚋属、厩螫蝇、沼泽大蚊;
鳞翅目,例如小蜡螟(Achroia grisella)、大蜡螟、印度谷螟(Plodiainterpunctella)、木塞谷蛾(Tinea cloacella)、袋谷蛾(Tineapellionella)、幕谷蛾(Tineola bisselliella);
膜翅目(Hymenoptera),例如广布弓背蚁(Camponotusherculeanus)、黑臭蚁(Lasius fuliginosus)、黑蚁(Lasius niger)、Lasius umbratus、小家蚁(Monomorium pharaonis)、Paravespulaspp.、铺道蚁(Tetramorium caespitum);
虱目(Anoplura),例如头虱、体虱、瘿绵蚜属、Phylloera vastatrix、阴虱;
异翅目,例如热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、长红猎蝽(Rhodinus prolixus)、侵扰锥猎蝽(Triatomainfestans)。
在卫生领域,本发明的施用可单独实施或与其它合适的活性成分如杀虫剂或杀菌剂一起实施,所述杀虫剂或杀菌剂优选为本文中提及的杀虫剂或杀菌剂,上述合适的活性成分选自磷酸酯、氨基甲酸酯、拟除虫菊酯、新烟碱类、生长调节剂。
一般而言,本发明的施用可以适合于施用形式的方式实施。合适的施用形式包括:气雾剂、无压喷雾剂例如泵压喷雾剂及雾化喷雾剂、自动弥雾系统、烟雾剂、泡沫剂、凝胶剂、具有由纤维素或聚合物制得的蒸发片的蒸发产品、液体蒸发器、凝胶和薄膜蒸发剂、推进剂驱动的蒸发剂、不消耗能量的蒸发系统(无源蒸发系统)、颗粒剂或粉末剂形式的捕蛾纸、捕蛾袋和捕蛾胶,以及用于抛撒的饵料或毒饵站。
特别地,本发明的活性化合物可被制成常规制剂形式。对于多种应用,尤其是农业领域和卫生领域中的应用,所述制剂形式——尤其是用作杀虫剂时——包括溶液、乳剂、可湿性粉剂、干悬浮剂、悬浮剂、粉剂、泡沫、膏剂、片剂、颗粒剂、气雾剂、活性化合物浸润的天然的和合成的产品、微胶囊剂、种衣剂、具有燃烧器(如熏蒸筒、熏蒸罐和熏蒸盘)的制剂、ULV(冷雾制剂)与热雾制剂。
这些制剂可通过本身已知的方式制备。例如将至少一种活性化合物与填充剂(developer)混合,即,与液体稀释剂或载体、液化气稀释剂或载体、或者固体稀释剂或载体混合,并任选使用表面活性剂(如阴离子、阳离子和非离子表面活性剂),具体为乳化剂和/或分散剂和/或发泡剂,从而制备所述制剂。
如果使用水作为填充剂,还可使用例如有机溶剂作为助溶剂。
合适的液体稀释剂或载体的实例可包括:芳香烃(例如二甲苯、甲苯和烷基萘)、氯代芳香族烃或氯代脂族烃(例如氯苯、氯乙烯和二氯甲烷)、脂族烃[例如环己烷、石蜡(例如矿物油馏分)]、醇(例如苯甲醇、异丙醇、乙醇、丁醇、乙二醇及它们的醚和酯)、酮(例如丙酮、甲乙酮、甲基异丁基酮和环己酮)、强极性溶剂(例如二甲基甲酰胺和二甲基亚砜);环状碳酸酯(例如碳酸亚乙酯、碳酸亚丙酯)、吡咯烷酮(例如N-辛基吡咯烷酮、N-甲基吡咯烷酮)、醚(例如二乙二醇单甲醚和二乙二醇单丙基醚)、内酯(例如丁内酯)以及水。
液化气稀释剂或载体的实例包括那些在常温常压为气体的稀释剂或载体,例如气溶胶喷射剂,如fron、丙烷、氮气、二氧化碳和卤代烃。
固体稀释剂的实例包括天然矿物粉(例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土)和合成矿物粉末(高度分散的二氧化硅、氧化铝和硅酸盐)。
适用于颗粒剂的固体载体的实例包括粉碎并分级的岩石(例如方解石、大理石、浮石、海泡石和白云石)、合成的无机或有机粉颗粒以及合成的有机物质颗粒(例如锯屑、椰壳、玉米穗轴和烟草茎)。
乳化剂和/或发泡剂的实例可包括非离子和阴离子乳化剂[例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚(例如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐]以及蛋白质水解产物。
分散剂包括木质素亚硫酸盐废液和甲基纤维素。
制剂中还可使用增粘剂(粉末、颗粒和乳油)。增粘剂的实例包括羧甲基纤维素、天然的或合成的聚合物(例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯)。
本发明中还可使用着色剂。着色剂的实例包括无机颜料(例如氧化铁、氧化钛和普鲁士蓝)、有机着色剂(如茜素着色剂、偶氮着色剂或金属酞菁着色剂,以及微量营养物,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐或锌盐。
制剂可含有通常占制剂总重量的0.1至95重量%的上述活性成分,优选0.5至90重量%。
在商业有益的制剂形式中和在由这些制剂制备的使用形式中,本发明的式(I)活性化合物可以与其它活性化合物的混合物的形式存在,例如杀虫剂、毒饵、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。此处,上述杀虫剂可包括有机磷试剂、碳酸酯试剂、羧酸酯类化学品、氯代烃类的化学品和由微生物制得的杀虫产品。
本发明的式(I)活性化合物可以与增效剂的混合物形式存在,其制备形式和使用形式的实例包括商业有益的形式。增效剂本身无需具有活性,并且此类化合物可增强活性化合物作用。
这些活性成分或增效剂为,例如以下物质:
起杀真菌剂作用的化合物:
核酸合成抑制剂,如苯霜灵(benalaxyl)、高效苯霜灵(benalaxyl-M)、磺嘧菌灵(bupirimate)、chiralaxyl、clozylacon、甲菌定(dimethirimol)、乙菌定(ethirimol)、呋氨丙灵(furalaxyl)、恶霜灵(hymexazol)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)和喹菌酮(oxolinic acid)。
有丝分裂和细胞分裂抑制剂,如苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuberidazole)、戊菌隆(pencycuron)、噻菌灵(thiabendazole)、甲基托布津(thiophanate-methyl)和苯酰菌胺(zoxamide)。
呼吸链复合体I抑制剂,如氟嘧菌胺(diflumetorim)。
呼吸链复合体II抑制剂,如啶酰菌胺(boscalid)、萎锈灵(carboxin)、甲呋酰胺(fenfuram)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、灭锈胺(mepronil)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)和噻氟唑菌(thifluzamide)。
呼吸链复合体III抑制剂,如嘧菌酯(azoxystrobin)、氰霜唑(cyazofamide)、醚菌胺(dimoxystrobin)、enestrobin、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、唑菌胺酯(pyraclostrobin)和啶氧菌酯(picoxystrobin)。
解偶联剂(decoupler),如敌螨普(dinocap)和氟啶胺(fluazinam)。
ATP生成抑制剂,如薯瘟锡(fentin acetate)、三苯锡氯(fentinchloride)、毒菌锡(fentin hydroxide)和硅噻菌胺(silthiofam)。
氨基酸生物合成和蛋白质生物合成抑制剂,如胺扑灭(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、春雷霉素水合盐酸盐(kasugamycin hydrochloride hydrate)、嘧菌胺(mepanipyrim)和嘧霉胺(pyrimethanil)。
信号转导抑制剂,如拌种咯(fenpiclonil)、咯菌腈(fludioxonil)和苯氧喹啉(quinoxyfen)。
脂类和膜合成抑制剂,如乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)、氨丙膦酸(ampropylfos)、氨丙膦酸钾(potassium ampropylfos)、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)(IBP)、稻瘟灵(isoprothiolane)、吡菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl)、联苯、iodocarb、霜霉威(propamocarb)和霜霉威盐酸盐(propamocarb hydrochloride)。
麦角甾醇生物合成抑制剂,如环酰菌胺(fenhexamide)、氧环唑(azaconazole)、联苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环丙唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、R-烯唑醇(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、四氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、灭菌唑(triticonazole)、烯效唑(uniconazole)、烯霜苄唑(voriconazole)、抑霉唑(imazalil)、烯菌灵(imazalil sulphate)、恶咪唑(oxpoconazole)、氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidole)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、稻瘟酯(pefurazoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、烯霜苯唑(viniconazole)、4-十二烷基-2,6-二甲基吗啉(aldimorph)、十二环吗啉(dodemorph)、吗菌灵(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)、苯锈啶(fenpropidin)、螺环菌胺(spiroxamine)、萘替芬(naftifin)、稗草丹(pyributicarb)和特比萘芬(terbinafine)。
细胞壁合成抑制剂,如苯噻菌胺(benthiavalicarb)、双丙氨膦(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)和有效霉素(validamycin A)。
黑色素生物合成抑制剂,如环丙酰菌胺(capropamide)、双氯氰菌胺(diclocymet)、氰菌胺(fenoxanil)、四氯苯酞(phthalid)、咯喹酮(pyroquilon)和三环唑(tricyclazole)。
抗性诱导剂,如苯并噻二唑(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)和噻酰菌胺(tiadinil)。
具有多位点活性的化合物,如敌菌丹(captafol)、克菌丹(captan)、百菌清(chlorothalonil)、铜盐:氢氧化铜、环烷酸铜、氧氯化铜、硫酸铜、氧化铜、喹啉铜(oxine-copper)以及波尔多液(Bordeaux mixture),苯氟磺胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodinefree base)、福美铁(ferbam)、氟灭菌丹(fluorofolpet)、双胍盐(guazatine)、双胍辛乙酸盐(guazatine acetate)、双胍辛胺(iminoctadine)、双八胍盐(iminoctadine albesilate)、双胍辛胺乙酸盐(iminoctadine triacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram、metiram zinc)、丙森锌(propineb)、硫和硫制剂包括多硫化钙、福美双(thiram)、甲苯氟磺胺(tolylfluanid)、代森锌(zineb)和福美锌(ziram)。
作用机理未知的化合物,如amibromdol、苯噻硫氰(benthiazole)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(quinoline methionat)、氯化苦(chloropicrin)、硫杂灵(cufraneb)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌酮(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、野燕枯(difenzoquat)、苯敌快(difenzoquat methyl sulfate)、二苯胺(diphenylamine)、噻唑菌胺(ethaboxam)、嘧菌腙(ferimzone)、氟酰菌胺(flumetover)、磺菌胺(flusulfamide)、氟吡菌胺(fluopicolide)、氟氯菌核利(fluoroimide)、六氯苯(hexachlorobenzene)、8-羟基喹啉(8-hydroxyquinoline sulfate)、人间霉素(irumamycin)、磺菌威(methasulfocarb)、苯菌酮(metrafenone)、异硫氰酸甲酯、米多霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickeldimethyldithiocarbamate)、酞菌酯(nitrothal-isopropyl)、辛噻酮(octhilinone)、oxamocarb、oxyfenthiin、五氯酚(pentachlorophenol)及其盐、2-苯基苯酚及其盐,病花灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、硝吡咯菌素(pyrrolnitrin)、五氯硝基苯(quintozen)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、咪唑嗪(triazoxide)、水杨菌胺(trichlamide)、氰菌胺(zarilamide),以及2,3,5,6-四氯-4-(甲磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、2,4-二氢-5-甲氧基-2-甲基-4-[[[[1-[3-(三氟甲基)苯基]亚乙基]氨基]氧基]甲基]苯基]-3H-1,2,3-三唑-3-酮(185336-79-2)、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基-[(4-甲氧基苯基)亚氨基]甲基]硫]甲基]-α-(甲氧基亚甲基)苯乙酸甲酯、4-氯-α-丙炔氧基-N-[2-[3-甲氧基-4-(2-丙炔氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺酰基)氨基]丁酰胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、N-[1-(5-溴-3-氯代吡啶-2-基)乙基]-2,4-二氯烟酰胺、N-(5-溴-3-氯代吡啶-2-基)甲基-2,4-二氯烟酰胺、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯乙酰胺、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰基氨基-2-羟基苯甲酰胺、2-[[[[1-[3-(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-αE-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯甲酰胺、N-(3′,4′-二氯-5-氟联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、N-(6-甲氧基-3-吡啶基)环丙甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-甲酸、O-{1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-硫代羟酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧亚氨基)-N-甲基乙酰胺。
起杀细菌剂作用的化合物,如溴硝醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福美镍、春雷霉素、辛噻酮、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracycline)、烯丙苯噻唑、链霉素(streptomycin)、叶枯酞、硫酸铜和其它铜制剂。
起杀昆虫剂和/或杀螨剂和/或杀线虫剂作用的化合物:
乙酰胆碱酯酶(AChE)抑制剂,如氨基甲酸酯类,例如,棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、合杀威(bufencarb)、畜虫威(butacarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、除线威(cloethocarb)、敌蝇威(dimetilan)、乙硫苯威(ethiofencarb)、丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、威百亩(metam-sodium)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、灭除威(XMC)、灭杀威(xylylcarb)和唑蚜威(triazamate);以及
有机磷酸酯类,例如,乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、保棉磷(azinphos-methyl)、益棉磷(azinphos-ethyl)、乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(bromfenvinfos(-methyl))、特嘧硫磷(autathiofos)、硫线磷(cadusafos)、三硫磷(carbophenothion)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、毒死蜱(chlorpyrifos-ethyl)、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏、甲基内吸磷(demeton-S-methyl)、砜吸磷(demeton-S-methylsulfone)、氯亚胺硫磷(dialifos)、二嗪磷(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫硫磷(fonofos)、安硫磷(formothion)、丁苯硫磷(fosmethilan)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、碘硫磷(iodofenphos)、异稻瘟净、氯唑磷(isazofos)、异柳磷(isofenphos)、O-水杨酸异丙酯、恶唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、甲基对硫磷(parathion-methyl)、对硫磷(parathion-ethyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、嘧啶磷(pirimiphos-ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、发硫磷(prothoate)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、哒硫磷(pyridathion)、喹硫磷(quinalphos)、硫线磷(sebufos)、治螟磷(sulfotep)、硫丙磷(sulprofos)、丁基嘧啶磷(tebupirimphos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)、蚜灭磷(vamidothion)。
钠通道调节剂/电位依赖性钠通道阻断剂,如拟除虫菊酯类,例如,氟酯菊酯(acrinathrin)、烯丙菊酯(d-顺-反,d-反)(allethrin(d-cis-trans,d-trans))、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、右旋反灭虫菊酯(bioresmethrin)、二氯炔戊菊酯(chlovaporthrin)、顺式氯氰菊酯(cis-cypermethrin)、顺式灭虫菊(cis-resmethrin)、顺式氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、氟丙苯醚(fubfenprox)、γ-氯氟氰菊酯(gamma-cyhalothrin)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(顺-、反-)、苯醚菊酯(1R-反式异构体)(phenothrin(1R trans-isomer)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、灭虫菊、RU 15525、氟硅菊酯(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R异构体)(tetramethrin(1R isomer))、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、ZXI 8901、除虫菊素(pyrethrin,pyrethrum);
DDT;噁二嗪类,例如茚虫威(indoxacarb)。
乙酰胆碱受体激动剂/拮抗剂,如氯烟碱基类(chloronicotinyl),例如,啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap)。
乙酰胆碱受体调节剂,如spinosyn类,例如多杀菌素(spinosad)。
GABA受控氯离子通道拮抗剂,如有机氯类,例如,毒杀芬(camphechlor)、氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、HCH、七氯(heptachlor)、林丹(lindane)、甲氧滴滴涕(methoxychlor);苯基吡唑类(fiprole),例如,acetoprole、乙虫腈(ethiprole)、氟虫腈(fipronil)、pyrafluprole、pyripole和氟吡唑虫(vaniliprole)。
氯离子通道活化剂类,如mectin类,例如,阿维菌素(avermectin)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectinbenzoate)、伊维菌素(ivermectin)、米尔倍霉素(milbemycin)、latidectin、lepimectin、selamectin、doramectin、eprinomectin以及moxidectin。
保幼激素模拟物类,例如,苯虫醚(diofenolan)、保幼醚(epofenonane)、苯氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene)、吡丙醚(pyriproxifen)以及烯虫硫酯(triprene)。
Latrophilin受体激动剂类,如酯肽类,优选环状酯肽,特别是24个原子的环状酯肽,例如emodepside。
蜕皮激素激动剂/干扰剂类(disruptor),如二酰基肼类,例如,环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)。
几丁质生物合成抑制剂,如苯甲酰脲类,例如,双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin);灭蝇胺(cyromazine)。
氧化磷酸化抑制剂,ATP干扰剂类,例如丁醚脲(diafenthiuron);有机锡类化合物,例如三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin-oxide)。
通过打断H-质子梯度而起作用的氧化磷酸化解偶联剂类,如吡咯类,例如虫螨腈(chlorfenapyr);二硝基苯酚类,例如乐杀螨(binapacryl)、消螨通(dinobuton)、敌螨普(dinocap)、DNOC。
位点-I电子转移抑制剂类,如METI类,例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad);灭蚁腙(hydramethylnon);三氯杀螨醇(dicofol)。
位点-II电子转移抑制剂类,如鱼藤酮(rotenone)。
位点-III电子转移抑制剂类,如灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)。
昆虫肠道膜微生物干扰剂类,如苏云金杆菌(Bacillus thuringiensis)菌株。
脂肪合成抑制剂类,如特窗酸类,例如,螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen);特特拉姆酸类,例如螺虫乙酯(spirotetramat,CAS注册号:203313-25-1)和3-(2,5-二甲基苯基)-8-甲氧基-2-氧杂-1-氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(别名:碳酸,3-(2,5-二甲基苯基)-8-甲氧基-2-氧杂-1-氮杂螺[4.5]癸-3-烯-4-基乙酯,CAS注册号:382608-10-8);甲酰胺类,例如氟啶虫酰胺(flonicamid)。
章鱼胺能激动剂类,例如双甲脒(amitraz)。
镁刺激ATP酶抑制剂类,如炔螨特(propargite)、苯甲酸二甲酰胺类,例如氟虫酰胺(flubendiamide);沙蚕毒素类似物,如杀虫环草酸盐(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)。
生物制剂类、激素类或信息素类,如印楝素(azadirachtin)、芽孢杆菌类(Bacillus spec.)、白僵菌类(Beauveria spec.)、十二碳二烯醇(codlemone)、绿僵菌属(Metarrhizium spec.)、拟青霉属(Paecilomyces spec.)、敌贝特(thuringiensin)、轮枝菌属(Verticilliumspec.)。
作用机理未知或不明确的活性化合物类,如熏蒸剂类,例如磷化铝、甲基溴、硫酰氟;拒食剂类,例如冰晶石(cryolite)、氟啶虫酰胺、吡蚜酮(pymetrozine);螨虫生长抑制剂类,例如四螨嗪(clofentezine)、乙螨唑(etoxazole)、噻螨酮(hexythiazox);amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、灭螨锰、杀虫脒(chlordimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦、clothiazoben、cycloprene、cyflumetofen、环虫腈(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、flubenzimine、flufenerim、氟螨嗪(flutenzin)、红铃虫性诱剂(gossyplure)、伏虫腙、japonilure、恶虫酮(metoxadiazone)、石油、增效醚(piperonyl butoxide)、油酸钾、啶虫丙醚(pyridalyl)、氟虫胺(sulfluramid)、三氯杀螨醇(tetradifon)、杀螨硫醚(tetrasul)、苯螨噻(triarathene)以及增效炔醚(verbutin)。
商业有益形式中的本发明式(I)活性化合物含量的浓度可在相当宽的范围内变化。
特别地,本发明式(I)活性化合物的浓度可在0.0000001至100重量%的范围内变化,优选在0.00001至1重量%的范围内变化,更优选在0.00001至0.5重量%的范围内变化。
根据本发明,式(I)化合物以一种常规的适合于使用形式的方法使用。施用以一种适合于使用形式的方式进行。
在农业领域中,即在植物保护领域中,所有的植物和植物部位可根据本发明进行处理。本发明中植物的含义应理解为所有的植物及植物种群,例如需要的及不需要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可为可通过常规植物培育和优选法或通过生物技术和遗传工程方法或通过前述方法的结合而获得的植物,包括转基因植物,也包括受植物种苗权保护或不受其保护的植物栽培种。植物部位的含义应理解为植物所有的地上及地下部位及器官,例如枝条、叶、花和根,可提及的实例为叶、针叶、茎、干、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收物以及无性与有性繁殖物,例如插枝、块茎、根茎、幼枝和种子。
根据本发明的使用本发明化合物对植物和植物部位进行的处理,通过常规处理方法直接进行或者通过使化合物作用于其所处环境、生境或储存空间来实现,所述常规处理方法例如浇灌(浸液)、滴灌、喷雾、蒸发、弥雾、撒播、喷撒、起泡、涂抹,并且作为干种子处理用粉剂、种子处理用溶液剂、种子处理用水溶性粉剂、浆料处理用水溶性粉剂,或者包壳,以及对于繁殖材料,尤其是种子,除干法处理、浆料处理、液体处理以外,还可包衣一层或多层。此外,还可通过超低容量法施用活性化合物,或者将活性化合物制剂或活性化合物本身注射进土壤。
本发明的化合物尤其适用于处理种子。大部分由害虫引起的对作物植物的侵害早在种子贮存的过程中、种子种入土壤后、以及植物发芽的过程中和植物刚发芽后受到侵袭时就已经发生了。由于正在生长的植物的根和芽特别敏感,即使微小的侵害也可导致整株植物的死亡,因此这一阶段非常关键。故而使用含有本发明化合物的合适组合物保护种子和正在发芽的植物非常有意义。
通过处理植物的种子防治害虫早已是公知的,并且是一个不断改进的主题。然而,种子处理经常会产生一系列并不能总是满意地解决的问题。因此,需要开发保护种子和发芽植物的方法,以避免在播种后或植物发芽后另外施用作物保护剂,或者至少大量地减少另外的施用。还需要优化活性化合物的用量,使所使用的活性化合物为种子和发芽植物提供最大保护,以使其免受害虫的侵害,而并不损害植物本身。具体而言,处理种子的方法还应考虑转基因植物的固有杀虫性能,以在使用最少的作物保护剂的情况下,达到对种子和发芽植物的最佳保护。
在农业领域中,在本发明处理方法中使用的活性化合物的剂量/施用率一般如下,对于叶部处理:0.1至10,000g/ha(公顷),优选10至1,000g/ha,更优选50至300g/ha;对于浸液或滴灌施用时,可降低剂量;对于种子处理:2至200g/100千克种子,优选3至150g/100千克种子;以及,对于土壤处理:0.1至10,000g/ha,优选1至5,000g/ha。
如上所述,可根据本发明处理所有的植物及其部位。在一个优选的实施方案中,处理了野生植物种和植物栽培种、或由常规生物育种方法例如杂交或原生质体融合获得的植物种和植物栽培种、以及所述植物种和植物栽培种的部位。在另一优选实施方案中,处理了由遗传工程方法、如果合适还可与常规方法相结合而获得的转基因植物和植物栽培种(遗传修饰生物)及其部位。术语“部位”、“植物的部位”和“植物部位”解释如上。
特别优选地,各自市售或现正使用的植物栽培种的植物依据本发明进行处理。植物栽培种的含义理解为由常规育种、诱变或重组DNA技术获得的具有新特性(“特征”)的植物。它们可以是栽培种、生物型(biotype)或基因型形式。
优选的依据本发明处理的(通过遗传工程方法获得的)转基因植物或植物栽培种包括通过遗传修饰而接受遗传物质的所有植物,所述遗传物质将特别有利的、有用的特征赋予所述植物。所述特征的实例有改善植物生长状况、提高高温或低温耐受性、提高对干旱或者对水中或土壤中含盐量的耐受性、提高开花品质、使采收更简易、加速成熟、提高采收产率、提高采收产品的品质和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。需特别强调的所述特征的其它实例有改善植物对动物有害物和有害微生物的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提出的转基因植物的实例为重要的作物植物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、甜菜、番茄、豌豆以及其它蔬菜品种、棉花、烟草、油菜和(果实为苹果、梨、柑橘类果实和葡萄)的果实植物,特别强调的是玉米、大豆、马铃薯、棉花、烟草和油菜。强调的特征特别是通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如由基因Cry I A(a)、Cry I A(b)、Cry I A(c)、Cry II A、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和Cry I F及其结合)在植物体内形成的毒素,来提高植物对昆虫、蛛形纲动物、线虫、蛞蝓和腹足类动物的抵抗力(以下简称为“Bt植物”)。还特别强调的特征为通过系统获得性抗性(SAR)、系统素、植物抗毒素、刺激素(elicitor)和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其强调的其它特征为提高植物对某些除草活性化合物例如咪唑啉酮类、磺酰脲类、草甘膦或草丁膦(phosphinotricin)(例如“PAT”基因)的耐受性。赋予所述所想要特征的基因也可各自在转基因植物体内相互结合存在。可提出的“Bt植物”的实例为市售的商标名称为(例如玉米、棉花、大豆)、(例如玉米)、(例如玉米)、(棉花)、(棉花)和(马铃薯)的玉米品种、棉花品种、大豆品种和马铃薯品种。可提出的具有除草剂耐受性的植物的实例为市售的商标名称为Roundup (具有草甘膦耐受性,例如玉米、棉花、大豆)、(具有草丁膦耐受性,例如油菜)、(具有咪唑啉酮耐受性)和(具有磺酰脲耐受性,例如玉米)的玉米品种、棉花品种和大豆品种。还可提出的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)包括名为的市售品种(例如玉米)。当然,以上叙述也适用于具有所述或待开发的遗传特征的植物栽培种,所述植物栽培种将在未来开发和/或上市。
所列植物可特别有利地用本发明的活性化合物处理。上述活性化合物的优选范围也适用于所述植物的处理。
当本发明的活性化合物用于卫生领域时,尤其是用于针对卫生害虫或贮存物质害虫时,它们对喜钙材料上的碱具有稳定性,并在木材和土壤中具有出色的残留效果。
下面,将通过实例更具体地阐述本发明,但并不想要将本发明限定至这些实施例。
合成实施例1(原料的合成)
将2-氟-5-甲酰基苄腈(1.0g,6.71mmol)和1H-1,2,4-三唑(0.56g,8.05mmol)溶于DMF。向该溶液中加入碳酸钾(1.1g,8.05mmol),并在120℃下搅拌6小时。将该反应溶液的温度降至室温,并向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯)获得0.60g5-甲酰基-2-(1H-1,2,4-三唑-1-基)苄腈(熔点:134-141℃,产率:43%)。
合成实施例2(原料的合成)
将5-甲酰基-2-(1H-1,2,4-三唑-1-基)苄腈(1.58g,7.97mmol)和盐酸羟胺(0.67g,9.57mmol)溶于THF-水(4:1)的混合溶剂中。向溶液中加入乙酸钠(0.92g,11.2mmol),室温下搅拌4小时。反应完成后,向反应溶液中加入水和乙酸乙酯以分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液,获得1.56g 5-[(肟基)甲基]-2-(1H-1,2,4-三唑-1-基)苄腈(熔点:198-200℃,产率:87%)。
合成实施例3
将N-氯琥珀酰亚胺(0.41g,3.04mmol)加入通过将5-[(肟基)甲基]-2-(1H-1,2,4-三唑-1-基)苄腈(0.59g,2.77mmol)溶于DMF而获得的混合物中,并将混合物搅拌2小时。再向混合物中加入1,3-二氯-5-[1-(三氟甲基)乙烯基]苯(0.82g,3.04mmol)。冰块冷却下,将溶于DMF中的三乙胺(0.31g,3.29mmol)逐滴加入上述混合物中。加入完成后,相同的温度下将所得的混合物搅拌2小时,然后在混合物的温度恢复至温室时再搅拌4小时。反应完成后,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.51g5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基)-2-(1H-1,2,4-三唑-1-基)苄腈(熔点:118-125℃,产率:39%)。
合成实施例4
将5-[3,5-二(三氟甲基)苯基]-3-(4-氟-3-硝基苯基)-5-(三氟甲基)-4,5-二氢异噁唑(0.40g,0.82mmol)和1H-四唑(0.09g,1.22mmol)溶解于DMF中。向溶液中加入碳酸钾(0.17g,1.25mmol),并在60℃下搅拌6小时。将反应溶液的温度降至室温,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.06g 1-(4-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}-2-硝基苯基)-2H-四唑(熔点:147-149℃,产率:13%)和0.28g 1-(4-{5-[3,5-二(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基}-2-硝基苯基)-1H-四唑(熔点:173-175℃,产率:60%)。
合成实施例5
将3-(4-氟-3-硝基苯基)-5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑(0.6g,1.42mmol)和1H-1,2,4-三唑(0.12g,1.70mmol)溶于DMF中。将碳酸钾(0.24g,1.70mmol)加入溶液中,并在60℃下搅拌6小时。将该反应溶液的温度降至室温,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.66g 1-{4-[5-[3,5-二氯苯基]-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-硝基苯基}-1H-1,2,4-三唑(熔点:64-72℃,产率:94%)。
合成实施例6
将1H-吡唑(0.06g,0.89mmol)溶于DMF中。在冰块冷却下,将氢化钠(60%,0.06g,0.89mmol)加入溶液中,然后将溶液的温度恢复至室温。搅拌溶液0.5小时并再次用冰块冷却。将溶于DMF中的5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-氟苄腈(0.30g,0.74mmol)逐滴加入混合物中。加入完成后,使反应溶液的温度回复至室温,并将溶液搅拌3小时。反应完成后,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.2g 5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-吡唑-1-基)苄腈(熔点:169-176℃,产率:57%)。
合成实施例7
将5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-吡唑-1-基)苄腈(0.43g,0.95mmol)溶解于DMF中。向该溶液中加入N-氯琥珀酰亚胺(0.14g,1.05mmol),然后在室温下搅拌2小时,以及在80℃下搅拌2小时。反应完成后,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.2g2-(4-氯-1H-吡唑-1-基)-5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苄腈(熔点:190-191℃,产率:41%)。
合成实施例8
将4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺(0.30g,0.80mmol)和2,5-二甲氧基四氢呋喃(0.26g,2.00mmol)溶解于乙酸中。将该溶液加热回流0.5小时。使反应溶液的温度回复至室温并向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.22g5-(3,5-二氯苯基)-3-[4-(1H-吡咯-1-基)苯基]-5-(三氟甲基)-4,5-二氢异噁唑(熔点:206-208℃,产率:61%)。
合成实施例9
将4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺(0.30g,0.80mmol)和1,2-二甲酰基肼(0.18g,2.00mmol)悬于吡啶中。在冰块冷却下,向悬浮液中顺序加入三乙胺(0.57g,5.6mmol)和三甲基氯硅烷(1.30g,12.0mmol)。之后,将液体加热回流4小时。使反应溶液的温度回复至室温,然后向反应溶液中加入水以获得沉淀物。将该沉淀物用少量的乙酸乙酯洗涤并干燥,获得0.14g4-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-4H-1,3,4-三唑(熔点>250℃,产率:39%)。
合成实施例10
将4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺(1.25g,3.33mmol)和三乙胺(0.40g,3.95mmol)溶于二氯甲烷中。在冰块冷却下,将三氟乙酸酐(0.80g,3.81mmol)的二氯甲烷溶液加入溶液中,并在室温下搅拌混合物1小时。反应完成后,将反应溶液用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液获得1.55g N-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-2,2,2-三氟乙酰胺(熔点:45-52℃,产率:99%)。
合成实施例11
将N-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-2,2,2-三氟乙酰胺(1.30g,2.76mmol)和三苯基膦(1.00g,3.81mmol)溶解于二氯甲烷中。30℃下向溶液中加入四氯化碳(0.60g,3.90mmol),并将所得的溶液加热回流5小时。反应完成后,通过在减压下浓缩反应溶液获得粗产物,用硅胶柱色谱(己烷/乙酸乙酯)纯化,获得1.20gN-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-2,2,2-三氟乙亚氨酸酰氯(产率:89%)。
合成实施例12
将N-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-2,2,2-三氟乙亚氨酸酰氯(0.125g,0.255mmol)溶解于乙腈中。向溶液中加入叠氮化钠(0.05g,0.769mmol),然后在室温下搅拌15小时。反应完成后,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。有机层用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.10g1-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-5-(三氟甲基)-1H-四唑(熔点:147-151℃,产率:79%)。
合成实施例13
将4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯胺(0.40g,1.07mmol)和原甲酸乙酯(0.30g,2.02mmol)溶解于乙酸中。向溶液中加入叠氮化钠(0.10g,1.54mmol),然后加热回流5小时。反应完成后,向溶液中加入水和乙酸乙酯来分离有机层,水层用乙酸乙酯萃取。有机层用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.25g1-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]苯基}-1H-四唑(熔点:198-199℃(分解),产率:55%)。
合成实施例14
将1-{4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-硝基苯基}-1H-1,2,4-三唑(0.53g,1.12mmol)和二水合氯化亚锡(1.01g,4.49mmol)悬于乙醇中。此外,向溶液中加入催化量的浓盐酸。将反应溶液在60℃下加热4小时。反应完成后,使反应溶液的温度回复至室温。向溶液中加入水和乙酸乙酯,然后在剧烈搅拌下用碳酸钾使其中和。使悬浮液经过Celite。分离有机层,并用乙酸乙酯萃取水层。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.38g5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)aniline(熔点:244-246℃,产率:73%)。
合成实施例15
将5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯胺(0.29g,0.66mmol)和吡啶(0.08g,0.98mmol)溶解于THF中。室温下向该溶液中加入乙酰氯(0.05g,0.69mmol),并搅拌1小时。反应完成后,向溶液中加入水和乙酸乙酯。分离有机层,并用乙酸乙酯萃取水层。合并有机层,用水洗涤并用无水硫酸镁干燥。通过过滤分离出干燥剂后,减压下浓缩滤液。所得粗产物用硅胶柱色谱纯化(己烷/乙酸乙酯),获得0.17g N-{5-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯基}乙酰胺(熔点:230-233℃,产率:51%)。
根据本发明以与原料合成以及终产物合成实施例相同的方式获得的式(I)化合物如表1所示,中间体的具体实例如表2至4所示。
在上述合成实施例中,对应于终产物的化合物如表1所示。
下表中,Me代表甲基,Et代表乙基,Prcyclo代表环丙基,Ph代表苯基。
表1
NMR分析
No.47
1H-NMR(CDCl3)δ:3.81(1H,d,J=17.4Hz),4.24(1H,d,J=17.4Hz),7.94(1H,d,J=8.3Hz),8.00(1H,s),8.08-8.16(4H,m),8.38(1H,s),8.89(1H,s).
No.80
1H-NMR(CDCl3)δ:3.80(1H,d,J=17.2Hz),4.12(1H,d,J=17.2Hz),7.50-7.58(5H,m),7.88-8.24(4H,m),8.87(1H,s).
No.98
1H-NMR(CDCl3)δ:3.72(1H,d,J=16.9Hz),4.10(1H,d,J=16.9Hz),7.47-7.84(5H,m),8.16(1H,s),8.26(1H,s),8.47(1H,s).
No.103
1H-NMR(CDCl3)δ:3.73(1H,d,J=17.2Hz),4.02(3H,s),4.12(1H,d,J=17.2Hz),7.21(1H,dd,J=8.2,1.6Hz),7.44-7.59(4H,m),7.95(1H,d,J=8.2Hz),8.09(1H,s),8.89(1H,s).
No.115
1H-NMR(CDCl3)δ:3.70(1H,d,J=17.4Hz),4.12(1H,d,J=17.4Hz),7.23-7.58(5H,m),8.22(1H,s),8.40(1H,s).
No.127
1H-NMR(CDCl3)δ:3.81(1H,d,J=17.4Hz),4.19(1H,d,J=17.4Hz),7.26-7.88(5H,m),8.09-8.24(3H,m),8.44(1H,s).
No.132
1H-NMR(CDCl3)δ:3.79(1H,d,J=17.2Hz),4.24(1H,d,J=17.2Hz),7.76-7.87(4H,m),7.97(1H,d,J=7.1Hz),8.12(3H,d,J=11.2Hz),8.62(1H,t,J=5.0Hz).
No.133
1H-NMR(CDCl3)δ:3.94(1H,d,J=17.0Hz),4.42(1H,d,J=17.0Hz),7.67-8.14(7H,m),8.60(1H,t,J=7.9Hz).
No.134
1H-NMR(CDCl3)δ:3.78(1H,d,J=17.0Hz),4.22(1H,d,J=17.0Hz),7.59-8.16(7H,m),8.60(1H,d,J=3.3Hz).
No.135
1H-NMR(CDCl3)δ:3.81(1H,d,J=17.2Hz),4.24(1H,d,J=17.2Hz),7.79-8.14(6H,m),8.22(1H,s),8.90(1H,s).
No.136
1H-NMR(CDCl3)δ:3.83(1H,d,J=17.3Hz),4.24(1H,d,J=17.3Hz),7.74(1H,d,J=8.4Hz),8.01(1H,s),8.09-8.16(4H,m),8.24(1H,d,J=1.8Hz),8.45(1H,s).
No.154
1H-NMR(CDCl3)δ:3.81(1H,d,J=17.3Hz),4.17(1H,d,J=17.3Hz),7.46-7.52(3H,m),7.74(1H,d,J=8.1Hz),8.20(1H,dd,J=1.9,8.2Hz),8.45(1H,d,J=1.9Hz),8.97(1H,s).
表2
表3
表4
生物学试验实施例1:
斜纹夜蛾(Spodoptera litura)幼虫试验
试验化学溶液的制备:
溶剂:3重量份的二甲基甲酰胺
乳化剂:1重量份的聚氧乙烯烷基苯基醚
为制备合适活性化合物的制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将混合物用水稀释至预定浓度。
试验方法:
将甘薯叶浸入已用水稀释至预定浓度的试验溶液中,然后将其风干以除去化学溶液,并将其放置于直径为9cm的皮氏培养皿中,该培养皿中释放了10只3龄的斜纹夜蛾幼虫。将皮氏培养皿放置在保持于25℃的恒温室中,并在2至4天后加入甘薯叶,以检测7天后死亡的幼虫数,由此计算出化学溶液的杀昆虫率。
本试验考察的是每组两个皮氏培养皿的平均结果。
试验结果:
上述生物学试验1中,上文所述的下列化合物作为典型实例在有效组分的浓度为500ppm时,产生了100%杀昆虫率的害虫防治作用:2、4、5、7、8、12、13、16、17、18、19、21、23、24、25、26、27、28、29、38、47、48、52、72、86、89、90、91、93、94、96、97、98、99、100、101、103、104、105、106、107、109、114、122、123、152、126、127、132、133、134、135、136、141、148、150、151、153、154、157、160、161、162、165、166、171、176、178和181。
生物学试验实施例2:
二斑叶螨(Tetranychusurticae)试验(喷雾试验)
试验方法
将50至100只成年的二斑叶螨接种于二叶期的黄豆叶上,该黄豆叶种植在直径为6cm的罐中。一天后,使用喷枪向其中充分地施用如上制备且用水稀释至预定浓度的活性化合物溶液。喷洒后,将叶置于温室中,7天后计算化学溶液的杀螨率。
试验结果:
有效组分浓度为100ppm时,上文所述的下列化合物作为典型实例产生了大于等于98%杀螨虫率的害虫防治作用:16、21、38、80、85、89、90、94、97、98、101、103、104、109、114、123、125、126、127、132、134、135、136、150、151、153、157、160、161、165和181。
生物学试验实施例3:
黄守瓜(Aulacophora femoralis)试验(喷雾试验)
试验方法
将黄瓜叶浸入已用水稀释至预定浓度的试验溶液中。使化学溶液风干后,将这些叶放置于包括无菌黑土的塑料杯中,向土壤中释放5只2龄的黄守瓜,以检测7天后死亡的昆虫数,由此计算出化学溶液的杀昆虫率。
试验结果:
上文所述的下列典型实例化合物在有效组分的浓度为500ppm时,产生了100%杀昆虫率的有害物防治作用:21、25、38、64、80、85、86、89、90、91、94、97、98、99、100、101、103、104、106、107、109、114、122、126、127、132、134、135、136、147、148、150、151、153、154、157、160、161、165、166、171和181。
生物学试验实施例4:
桃蚜(Myzus persicas)对有机磷试剂和氨基甲酸酯类试剂的抗性试验
试验方法
对应于每颗幼苗约200只培育的有机磷抗性和氨基甲酯抗性的桃蚜接种于茄苗上。接种一天后,使用喷枪向茄苗上充分地施用含有如上制备且具有特定浓度的活性化合物的水溶液,并将茄苗置于28℃的温室中。喷洒24小时后计算杀昆虫率。将该试验重复2次。
试验结果:
上文所述的下列典型实例化合物在有效组分的浓度为500ppm时,产生了100%杀昆虫率的害虫防治作用:38、101、135和153。
生物学试验实施例5:
铜绿蝇(Lucilia cuprina)幼虫试验
将20mg活性化合物溶解于1ml二甲基亚砜中。为制备合适的制剂(例如100ppm),用水将活性化合物溶液分别稀释至想要的浓度(例如1重量份的活性化合物溶液与199重量份的水)。
将约20头铜绿蝇幼虫引入含有约1cm3的马肉和0.5ml待测活性化合物制剂的试管中。48小时后,以%幼虫死亡率确定活性化合物制剂的功效。0%:没有幼虫被杀死,100%所有幼虫均被杀死。
该试验中,以下化合物在100ppm下2天后显示出>95%的幼虫死亡率:8、9、12、14、16、17、18、19、20、30、36、38、40、42、43、44、45、46、54、55、58、59、60、61、62、63、66、67、68、70、80、88、89、91、93、94、76、77、78、82、71、72、73、75、84。
生物学试验实施例6:
家蝇(Musca domestica)试验
将20mg活性化合物溶解于1ml二甲基亚砜中。为制备合适的制剂,(如100ppm),用水将活性化合物溶液分别稀释至想要的浓度(例如1重量份的活性化合物溶液与199重量份的水)。
将0.2ml活性化合物制剂吸入用0.8ml糖溶液湿润的海绵(直径约1.5cm)上。将海绵和10只受试的动物转移至小盘(4 x 4cm,高2cm)中并盖上。
48小时后确定活性化合物制剂的活性。此处100%是指所有的蝇被杀死;0%是指没有蝇被杀死。
该试验中,以下化合物在100ppm下2天后显示出>95%的幼虫死亡率:8、9、14、16、18、19、20、30、36、40、42、43、44、45、46、55、58、60、61、62、66、67、68、70、80、88、89、91、93、94、76、77、78、82、71、72、73、75、84。
生物学试验实施例7:
猫蚤(Cat fleas)试验/口服
将20mg活性化合物溶解于1ml二甲基亚砜中。为制备合适的制剂,(如100ppm),用牛血将活性化合物溶液分别稀释至想要的浓度(例如1重量份的活性化合物溶液与199重量份的牛血)。
将20头未喂食的蚤猫栉首蚤(Ctenocephalides felis,“Georgi”系)成虫放置在小室中(直径为5cm),其顶部和底部用纱布覆盖。将底部用薄膜盖住的金属圆筒放置在小室上。该圆筒内含有血液/活性化合物制剂,其可通过膜被蚤吸收。将血液升温至37℃,蚤所在的区域的温度被调节至室温。
所需时间后,确定以%计的死亡率。此处100%表示所有的蚤被杀死;0%表示没有蚤被杀死。
该试验中,以下化合物在100ppm下2天后产生>80%的死亡率:8、9、12、14、16、17、18、19、20、30、36、38、40、42、43、44、54、58、60、61、62、66、67、80、88、89、91、93、94、76、77、78、82、71、72、73、75、84。
生物学试验实施例8:
微小牛蜱(Rhipicephalus(Boophilus)microplus)试验;注射
将20mg活性化合物溶解于1ml二甲基亚砜中。更低浓度的制剂通过将用相同的溶剂稀释制备。
该试验使用从宿主上掉落不超过24小时采集的充分充血的雌性牛蜱平行五份进行。将1μl溶液注射进下腹部,并将蜱转移至相同的盘中并储存在环境可控的小室内。活性通过7天后受精卵的沉积量确定。从外部无法辨别是否受精的卵被储存在环境可控的小室的玻璃管中,直到约42天后孵化出幼虫。100%活性表示没有蜱产出受精卵。
该实验中,以下化合物在20μg/蜱时,7天后产生>90%的活性:8、9、12、14、16、17、18、20、30、36、38、40、42、43、44、45、46、63、66、67、68、70、80、88、89、91、93、94、76、77、78、82、71、72、73、75、84。
制剂实施例1(颗粒剂)
将25份水加入10份本发明的化合物(26)、30份膨润土(蒙脱石)、58份滑石和2份木质素磺酸盐的混合物中,并将所得的混合物充分揉合通过挤出型制粒机制成10至40目的颗粒形式,然后在40至50℃下干燥以形成颗粒剂。
制剂实施例2(颗粒剂)
将95份粒径分布为0.2至2mm的粘土矿物质颗粒放入滚筒搅拌机中。在搅拌机旋转时,将5份本发明的化合物(72)与液体稀释剂一起喷洒,以使颗粒均匀润湿,然后40至50℃干燥以形成颗粒剂。
制剂实施例3(乳油)
将30份本发明的化合物(107)、55份的二甲苯、8份聚氧乙烯烷基苯基醚和7份烷基苯磺酸钙混合并搅拌以制备乳油。
制剂实施例4(可湿性粉剂)
将15份本发明的化合物(91)、80份由1:5的白炭(含水的无定形二氧化硅粉末)和粉状粘土组成的混合物、2份烷基苯基磺酸钠和3份烷基萘磺酸钠-福尔马林缩合物研磨并混合,以制备可湿性粉剂。
制剂实施例5(干悬浮剂)
将20份本发明的化合物(114)、30份木质素磺酸钠、15份膨润土和35份锻制硅藻土完全混合。向混合物中加入水,然后通过0.3mm的筛挤出并干燥,以形成干悬浮剂。
Claims (19)
3.权利要求1或2的化合物,其中
A 代表C或N;
R 代表三氟甲基或五氟乙基;
X 彼此独立地代表氟、氯、溴或三氟甲基;
l 代表0、1或2;
Y 彼此独立地代表卤素、C1-2烷基、C1-2烷氧基、C1-2卤代烷基、氰基、硝基、氨基、C1-2烷基-羰基氨基、环丙基羰基氨基、苯甲酰基氨基、C1-2烷氧基-羰基氨基或C1-2烷基-磺酰基氨基;
m 代表0、1或2;并且
G 选自由式G-1至G-9表示的杂环基:
其中
Z 代表卤素、甲基、甲硫基、三氟甲基、氰基、硝基或氨基;并且
n 代表0或1。
4.组合物,包括至少一种用于防治有害昆虫的式(I)化合物。
5.防治有害昆虫的方法,其特征在于使权利要求1至4之一的至少一种化合物或组合物作用于有害昆虫和/或其生境。
6.权利要求1至4之一的化合物或组合物的用途,用于防治有害昆虫。
7.权利要求1至3之一的化合物的用途,用于制备一种防治动物寄生虫的组合物。
8.权利要求7的用途,其中所述动物寄生虫是寄生性节肢动物。
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