CN105051045B - 稠杂环化合物或其盐类和含有该化合物的农业园艺用杀虫剂及其使用方法 - Google Patents
稠杂环化合物或其盐类和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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- CN105051045B CN105051045B CN201480016043.7A CN201480016043A CN105051045B CN 105051045 B CN105051045 B CN 105051045B CN 201480016043 A CN201480016043 A CN 201480016043A CN 105051045 B CN105051045 B CN 105051045B
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
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- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
在农业和园艺等的作物生产中,因害虫等而遭受的灾害目前仍很严重,因此,本发明的课题在于从对现有药剂具有抗性的害虫的产生等主要原因出发,开发、提供新的农业园艺用杀虫剂。本发明提供通式(I){式中,A1、A2、A3可以相同或不同,表示氮原子或CH基,R1表示烷基等,R2表示卤代烷基等,R3表示氢原子等,R4表示卤代烷基等,R5表示烷基等,m表示0或2}所示的稠杂环化合物或其盐类、以该稠杂环化合物或其盐类作为有效成分的农业园艺用杀虫剂以及其使用方法。
Description
技术领域
本发明涉及以某种稠杂环化合物或其盐类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
到目前为止,作为农业园艺用杀虫剂,对各种各样的化合物进行了研究,已经报道了某种稠杂环化合物作为杀虫剂是有用的(例如,参考专利文献1~6)。该文献中未公开包含哒嗪环的稠杂环化合物。
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号小册子
专利文献6:国际公开第2013/018928号小册子
发明内容
发明所要解决的问题
在农业和园艺等的作物生产中,因害虫等而遭受的灾害目前仍很严重,从对现有药剂具有抗性的害虫的产生等主要原因出发,期望开发新的农业园艺用杀虫剂。
用于解决问题的方法
本发明人为了解决上述问题进行了潜心研究,结果发现,通式(I)所示的稠杂环化合物或其盐类对农业园艺用害虫具有优良的防除效果,从而完成了本发明。
即,本发明涉及:
[1]通式(I)所示的稠杂环化合物及其盐类,
{式中,R1表示(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a6)卤代(C3-C6)环烷基;
(a7)卤代(C2-C6)链烯基;
(a8)卤代(C2-C6)炔基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a12)卤代(C3-C6)环烷基(C1-C6)烷基;
(a13)(C1-C6)烷氧基卤代(C1-C6)烷基;
(a14)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a16)(C1-C6)烷基亚磺酰基(C1-C6)烷基;
(a17)(C1-C6)烷基磺酰基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基(二(C1-C6)烷基氨基的烷基可以相同或不同);
(a21)苯基(C1-C6)烷基;或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2表示
(b1)卤素原子;
(b2)氰基;
(b3)硝基;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b9)卤代(C3-C6)环烷基;
(b10)卤代(C2-C6)链烯基;
(b11)卤代(C2-C6)炔基;
(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(C1-C6)烷基;
(b19)卤代(C1-C6)烷氧基(C1-C6)烷基;
(b20)(C3-C6)环烷基(C1-C6)烷基;
(b21)卤代(C3-C6)环烷基(C1-C6)烷基;
(b22)(C1-C6)烷氧基卤代(C1-C6)烷基;
(b23)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(b24)氢原子;
(b25)(C1-C6)烷氧基;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b28)(C1-C6)烷基氨基;
(b29)二(C1-C6)烷基氨基(二(C1-C6)烷基的烷基可以相同也可以不同);
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(三(C1-C6)烷基甲硅烷基的烷基可以相同也可以不同);
R3表示
(c1)氢原子;
(c2)卤素原子;
(c3)氰基;
(c4)硝基;
(c5)(C1-C6)烷基;
(c6)(C1-C6)烷氧基;
(c7)(C2-C6)链烯基氧基;
(c8)(C2-C6)炔基氧基;
(c9)卤代(C1-C6)烷基;
(c10)卤代(C1-C6)烷氧基;
(c11)卤代(C2-C6)链烯基氧基;
(c12)卤代(C2-C6)炔基氧基;
(c13)(C1-C6)烷氧基(C1-C6)烷基;
(c14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(c15)(C3-C6)环烷基(C1-C6)烷基;
(c16)卤代(C3-C6)环烷基(C1-C6)烷基;
(c17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(c18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
R4表示
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)硝基;
(d5)(C1-C6)烷基;
(d6)(C1-C6)烷氧基;
(d7)(C2-C6)链烯基氧基;
(d8)(C2-C6)炔基氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)卤代(C2-C6)链烯基氧基;
(d12)卤代(C2-C6)炔基氧基;
(d13)(C1-C6)烷氧基(C1-C6)烷基;
(d14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d15)(C3-C6)环烷基(C1-C6)烷基;
(d16)卤代(C3-C6)环烷基(C1-C6)烷基;
(d17)(C1-C6)烷氧基卤代(C1-C6)烷基;
(d18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d23)苯基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;
(d25)(C1-C6)烷基亚磺酰基;
(d26)(C1-C6)烷基磺酰基;
(d27)卤代(C1-C6)烷基亚磺酰基;或
(d28)卤代(C1-C6)烷基磺酰基;
R5表示
(e1)氢原子;
(e2)甲酰基;
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e6)卤代(C3-C6)环烷基;
(e7)(C1-C6)烷基磺酰基;
(e8)卤代(C1-C6)烷基磺酰基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(e11)(C1-C6)烷氧基卤代(C1-C6)烷基;
(e12)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(e13)氨基;或
(e14)(C1-C6)烷氧基。
A1、A2和A3可以相同或不同,表示氮原子或C-R6基(在此,R6表示
(f1)氢原子;
(f2)卤素原子;
(f3)氰基;
(f4)硝基;
(f5)甲酰基;
(f6)(C1-C6)烷基;
(f7)(C1-C6)烷氧基;
(f8)(C2-C6)链烯基氧基;
(f9)(C2-C6)炔基氧基;
(f10)(C3-C6)环烷氧基;
(f11)卤代(C1-C6)烷基;
(f12)卤代(C1-C6)烷氧基;
(f13)卤代(C2-C6)链烯基氧基;
(f14)卤代(C2-C6)炔基氧基;
(f15)卤代(C3-C6)环烷氧基;
(f16)(C1-C6)烷硫基;
(f17)(C1-C6)烷基亚磺酰基;
(f18)(C1-C6)烷基磺酰基;
(f19)卤代(C1-C6)烷硫基;
(f20)卤代(C1-C6)烷基亚磺酰基;
(f21)卤代(C1-C6)烷基磺酰基;
(f22)(C1-C6)烷氧基(C1-C6)烷基;
(f23)卤代(C1-C6)烷氧基(C1-C6)烷基;
(f24)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(f25)卤代(C1-C6)烷氧基卤代(C1-C6)烷基)。
m表示0、1或2。}。
[2]如上述[1]所述的稠杂环化合物及其盐类,其中,
R1为
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a16)(C1-C6)烷基亚磺酰基(C1-C6)烷基;
(a17)(C1-C6)烷基磺酰基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基(二烷基氨基的烷基可以相同或不同);
(a21)苯基(C1-C6)烷基;或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为
(b1)卤素原子;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b12)(C1-C6)烷硫基;
(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;
(b24)氢原子;
(b25)(C1-C6)烷氧基;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b29)二(C1-C6)烷基氨基(二(C1-C6)烷基的烷基可以相同也可以不同);
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(三(C1-C6)烷基甲硅烷基的烷基可以相同也可以不同);
R3为(c1)氢原子;
R4为
(d2)卤素原子;
(d5)(C1-C6)烷基;
(d9)卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或
(d26)(C1-C6)烷基磺酰基;
R5为
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e13)氨基;或
(e14)(C1-C6)烷氧基;
A1、A2和A3可以相同或不同,为氮原子或C-R6基(在此,R6为(f1)氢原子)。
[3]如上述[1]所述的稠杂环化合物及其盐类,其中,
R1为
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a5)卤代(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基(二(C1-C6)烷基氨基的烷基可以相同或不同);或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为
(b1)卤素原子;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b12)(C1-C6)烷硫基;
(b15)卤代(C1-C6)烷硫基;
(b24)氢原子;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b29)二(C1-C6)烷基氨基(二(C1-C6)烷基的烷基可以相同也可以不同);
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(三(C1-C6)烷基甲硅烷基的烷基可以相同也可以不同);
R3为(c1)氢原子;
R4为
(d2)卤素原子;
(d9)卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或
(d26)(C1-C6)烷基磺酰基;
R5为
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;或
(e9)(C1-C6)烷氧基(C1-C6)烷基;
A1、A2和A3可以相同或不同,为氮原子或C-R6基(在此,R6为(f1)氢原子)。
[4]上述[1]~[3]中任一项所述的稠杂环化合物或其盐类作为农业园艺用杀虫剂的使用。
[5]一种农业园艺用杀虫剂的使用方法,其特征在于,使用上述[4]所述的农业园艺用杀虫剂的有效成分对植物或土壤进行处理。
[6]一种农业园艺用害虫的防除方法,其特征在于,使用有效量的上述[4]所述的农业园艺用杀虫剂对植物或土壤进行处理。
[7]一种外寄生物防除剂,其特征在于,含有上述[1]~[3]中任一项所述的稠杂环化合物或其盐类作为有效成分。
[8]一种外寄生物的防除方法,其特征在于,使用有效量的上述[7]所述的外寄生物防除剂对外寄生物进行处理。
[9]一种杀虫剂,其含有通式(I)或其盐所例示的咪唑并哒嗪稠杂环化合物作为有效成分。
[10]如上述[9]所述的杀虫剂,其中,咪唑并哒嗪稠杂环化合物为咪唑并[4,5-C]哒嗪稠杂环化合物。
或者,
[11]通式(I)所示的稠杂环化合物及其盐类,
{式中,
R1表示
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a6)卤代(C3-C6)环烷基;
(a7)卤代(C2-C6)链烯基;
(a8)卤代(C2-C6)炔基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a12)卤代(C3-C6)环烷基(C1-C6)烷基;
(a13)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(a14)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R2表示
(b1)卤素原子;
(b2)氰基;
(b3)硝基;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b9)卤代(C3-C6)环烷基;
(b10)卤代(C2-C6)链烯基;
(b11)卤代(C2-C6)炔基;
(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(C1-C6)烷基;
(b19)卤代(C1-C6)烷氧基(C1-C6)烷基;
(b20)(C3-C6)环烷基(C1-C6)烷基;
(b21)卤代(C3-C6)环烷基(C1-C6)烷基;
(b22)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(b23)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R3表示
(c1)氢原子;
(c2)卤素原子;
(c3)氰基;
(c4)硝基;
(c5)(C1-C6)烷基;
(c6)(C1-C6)烷氧基;
(c7)(C2-C6)链烯基氧基;
(c8)(C2-C6)炔基氧基;
(c9)卤代(C1-C6)烷基;
(c10)卤代(C1-C6)烷氧基;
(c11)卤代(C2-C6)链烯基氧基;
(c12)卤代(C2-C6)炔基氧基;
(c13)(C1-C6)烷氧基(C1-C6)烷基;
(c14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(c15)(C3-C6)环烷基(C1-C6)烷基;
(c16)卤代(C3-C6)环烷基(C1-C6)烷基;
(c17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(c18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R4表示
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)硝基;
(d5)(C1-C6)烷基;
(d6)(C1-C6)烷氧基;
(d7)(C2-C6)链烯基氧基;
(d8)(C2-C6)炔基氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)卤代(C2-C6)链烯基氧基;
(d12)卤代(C2-C6)炔基氧基;
(d13)(C1-C6)烷氧基(C1-C6)烷基;
(d14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d15)(C3-C6)环烷基(C1-C6)烷基;
(d16)卤代(C3-C6)环烷基(C1-C6)烷基;
(d17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(d18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R5表示
(e1)氢原子;
(e2)甲酰基;
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e6)卤代(C3-C6)环烷基;
(e7)(C1-C6)烷基磺酰基;
(e8)卤代(C1-C6)烷基磺酰基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(e11)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(e12)卤代(C1-C6)烷氧基卤代(C1-C6)烷基。
A1、A2和A3可以相同或不同,表示氮原子或C-R6基(在此,R6表示
(f1)氢原子;
(f2)卤素原子;
(f3)氰基;
(f4)硝基;
(f5)甲酰基;
(f6)(C1-C6)烷基;
(f7)(C1-C6)烷氧基;
(f8)(C2-C6)链烯基氧基;
(f9)(C2-C6)炔基氧基;
(f10)(C3-C6)环烷氧基;
(f11)卤代(C1-C6)烷基;
(f12)卤代(C1-C6)烷氧基;
(f13)卤代(C2-C6)链烯基氧基;
(f14)卤代(C2-C6)炔基氧基;
(f15)卤代(C3-C6)环烷氧基;
(f16)(C1-C6)烷硫基;
(f17)(C1-C6)烷基亚磺酰基;
(f18)(C1-C6)烷基磺酰基;
(f19)卤代(C1-C6)烷硫基;
(f20)卤代(C1-C6)烷基亚磺酰基;
(f21)卤代(C1-C6)烷基磺酰基;
(f22)(C1-C6)烷氧基(C1-C6)烷基;
(f23)卤代(C1-C6)烷氧基(C1-C6)烷基;
(f24)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(f25)卤代(C1-C6)烷氧基卤代(C1-C6)烷基)。
m表示0、1或2。}。
[12]如上述[11]所述的稠杂环化合物及其盐类,其中,
R1为(a1)(C1-C6)烷基;
R2为
(b1)卤素原子;
(b4)(C1-C6)烷基;或
(b8)卤代(C1-C6)烷基;
R3为(c1)氢原子;
R4为(d9)卤代(C1-C6)烷基;
R5为
(e3)(C1-C6)烷基;或
(e4)(C3-C6)环烷基,
A1、A2和A3为C-R6基(在此,R6为(f1)氢原子),
m为0或2。
[13]如上述[11]所述的稠杂环化合物及其盐类,其中,
R1为(a1)(C1-C6)烷基;
R2为(b8)卤代(C1-C6)烷基;
R3为(c1)氢原子;
R4为(d9)卤代(C1-C6)烷基;
R5为(e3)(C1-C6)烷基;
A1、A2和A3为C-R6基(在此,R6为(f1)氢原子),
m为0或2。
[14]上述[11]~[13]中任一项所述的稠杂环化合物或其盐类作为农业园艺用杀虫剂的使用。
[15]一种农业园艺用杀虫剂的使用方法,其特征在于,使用上述[14]所述的农业园艺用杀虫剂的有效成分对植物或土壤进行处理。
[16]一种农业园艺用害虫的防除方法,其特征在于,使用有效量的上述[14]所述的农业园艺用杀虫剂对植物或土壤进行处理。
[17]一种外寄生物防除剂,其特征在于,含有上述[11]~[13]中任一项所述的稠杂环化合物或其盐类作为有效成分。
[18]一种外寄生物的防除方法,其特征在于,使用有效量的上述[17]所述的外寄生物防除剂对外寄生物进行处理。
[19]一种杀虫剂,其含有通式(I)或其盐所例示的咪唑并哒嗪稠杂环化合物作为有效成分。
[20]如上述[19]所述的杀虫剂,其中,咪唑并哒嗪稠杂环化合物为咪唑并[4,5-C]哒嗪稠杂环化合物。
发明效果
本发明的稠杂环化合物或其盐类不仅作为农业园艺用杀虫剂具有优良的效果,而且对寄生在狗、猫等玩赏动物或者牛、羊等家畜的体外或体内的害虫也具有效果。
具体实施方式
本发明的稠杂环化合物或其盐类的通式(I)的定义中,“卤代”是指“卤素原子”,表示氯原子、溴原子、碘原子或氟原子。
“(C1-C6)烷基”表示例如甲基、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)链烯基”表示例如乙烯基、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个的链烯基,“(C2-C6)炔基”表示例如乙炔基、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”表示例如环丙基、环丁基、环戊基、环己基等碳原子数为3~6个的环状烷基,作为“(C1-C6)烷氧基”,表示例如甲氧基、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,作为“(C2-C6)链烯基氧基”,表示例如丙烯基氧基、丁烯基氧基、戊烯基氧基、己烯基氧基等直链或支链状的碳原子数为2~6个的链烯基氧基,作为“(C2-C6)炔基氧基”,表示例如丙炔基氧基、丁炔基氧基、戊炔基氧基、己炔基氧基等直链或支链状的碳原子数为2~6个的炔氧基。
作为“(C1-C6)烷硫基”,表示例如甲硫基、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,作为“(C1-C6)烷基亚磺酰基”,表示例如甲基亚磺酰基、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,作为“(C1-C6)烷基磺酰基”,表示例如甲基磺酰基、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。
作为“(C2-C6)链烯基硫基”,表示例如丙烯基硫基、丁烯基硫基、戊烯基硫基、己烯基硫基等直链或支链状的碳原子数为2~6个的链烯基硫基,作为“(C2-C6)炔基硫基”,表示例如丙炔基硫基、丁炔基硫基、戊炔基硫基、己炔基硫基等直链或支链状的碳原子数为2~6个的炔基硫基。
作为“(C2-C6)链烯基亚磺酰基”,表示例如丙烯基亚磺酰基、丁烯基亚磺酰基、戊烯基亚磺酰基、己烯基亚磺酰基等直链或支链状的碳原子数为2~6个的链烯基亚磺酰基,作为“(C2-C6)炔基亚磺酰基”,表示例如丙炔基亚磺酰基、丁炔基亚磺酰基、戊炔基亚磺酰基、己炔基亚磺酰基等直链或支链状的碳原子数为2~6个的炔基亚磺酰基。
作为“(C2-C6)链烯基磺酰基”,表示例如丙烯基磺酰基、丁烯基磺酰基、戊烯基磺酰基、己烯基磺酰基等直链或支链状的碳原子数为2~6个的链烯基磺酰基,作为“(C2-C6)炔基磺酰基”,表示例如丙炔基磺酰基、丁炔基磺酰基、戊炔基磺酰基、己炔基磺酰基等直链或支链状的碳原子数为2~6个的炔基磺酰基。
“(C3-C6)环烷氧基”表示例如环丙氧基、环丁氧基、环戊氧基、环己氧基等碳原子数为3~6个的环状烷氧基,“(C3-C6)环烷硫基”表示例如环丙硫基、环丁硫基、环戊硫基、环己硫基等碳原子数为3~6个的环状烷硫基,“(C3-C6)环烷基亚磺酰基”表示例如环丙基亚磺酰基、环丁基亚磺酰基、环戊基亚磺酰基、环己基亚磺酰基等碳原子数为3~6个的环状烷基亚磺酰基,“(C3-C6)环烷基磺酰基”表示例如环丙基磺酰基、环丁基磺酰基、环戊基磺酰基、环己基磺酰基等碳原子数为3~6个的环状烷基磺酰基。
“苯基(C1-C6)烷基”是指上述(C1-C6)烷基的一个氢原子被苯基取代的基团,可以列举例如苯基甲基(苄基)、苯基乙基(苯乙基)、苯基丙基等。
“在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基”是指,上述苯基(C1-C6)烷基中的苯基的1~5个氢原子各自独立地被选自由上述(a)~(g)组成的组中的取代基取代的基团。
“(C1-C6)烷氧基羰基”是指具有上述(C1-C6)烷氧基的烷氧基羰基、即碳原子数为2~7的烷氧基羰基,可以列举例如甲氧基羰基、乙氧基羰基、丙氧基羰基、异丙氧基羰基、丁氧基羰基、异丁氧基羰基、叔丁氧基羰基、戊氧基羰基等。
“(C1-C6)烷氧基羰基氧基”是指具有上述(C1-C6)烷氧基羰基的氧基。
“二(C1-C6)烷基氨基”是指例如被相同或不同的上述(C1-C6)烷基双取代的氨基,可以列举例如二甲基氨基、二乙基氨基、乙基甲基氨基、二丙基氨基、甲基丙基氨基、二异丙基氨基等。
“(C1-C6)烷基羰基硫基”是指具有(C1-C6)烷基羰基的硫基。另外,“(C1-C6)烷基羰基”是指具有上述(C1-C6)烷基的烷基羰基、即碳原子数为2~7的烷基羰基,可以列举例如乙酰基、丙酰基、丁酰基、2-甲基丙酰基、戊酰基、2-甲基丁酰基、3-甲基丁酰基、特戊酰基、己酰基、环丙基羰基等。
“(C1-C6)烷基羰基氨基”是指被(C1-C6)烷基羰基取代的氨基。(C1-C6)烷基羰基可以与上述“(C1-C6)烷基羰基硫基”中的“(C1-C6)烷基羰基”含义相同。
“(C1-C6)烷基磺酰基氨基”是指被上述(C1-C6)烷基磺酰基取代的氨基。
“(C1-C6)烷基磺酰基((C1-C6)烷基)氨基”是指被(C1-C6)烷基磺酰基和(C1-C6)烷基取代的氨基。(C1-C6)烷基磺酰基和(C1-C6)烷基可以为与上述相同的含义。
“三(C1-C6)烷基甲硅烷基(C2-C6)炔基”是指被“三(C1-C6)烷基甲硅烷基”取代的上述(C2-C6)炔基。另外,“三(C1-C6)烷基甲硅烷基”是指被相同或不同的上述(C1-C6)烷基三取代的甲硅烷基,可以列举例如三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙基二甲基甲硅烷基、异丙基二甲基甲硅烷基、正丙基二甲基甲硅烷基等。
在上述“(C1-C6)烷基”、“(C2-C6)链烯基”、“(C2-C6)炔基”、“(C3-C6)环烷基”、“(C3-C6)环烷氧基”、“(C1-C6)烷氧基”、“(C2-C6)链烯基氧基”、“(C2-C6)炔基氧基”、“(C1-C6)烷硫基”、“(C1-C6)烷基亚磺酰基”、“(C1-C6)烷基磺酰基”、“(C2-C6)链烯基硫基”、“(C2-C6)炔基硫基”、“(C2-C6)链烯基亚磺酰基”、“(C2-C6)炔基亚磺酰基”、“(C2-C6)链烯基磺酰基”、“(C2-C6)炔基磺酰基”、“(C3-C6)环烷硫基”、“(C3-C6)环烷基亚磺酰基”、“(C3-C6)环烷基磺酰基”、“(C1-C6)烷氧基羰基氧基”、“二(C1-C6)烷基氨基”或“(C1-C6)烷基羰基硫基”的可取代的位置,可以取代有1个或2个以上的卤素原子,在取代的卤素原子为2个以上的情况下,卤素原子可以相同或不同。
上述的“在可取代的位置取代有1个或2个以上的卤素原子的取代基”分别表示为“卤代(C1-C6)烷基”、“卤代(C2-C6)链烯基”、“卤代(C2-C6)炔基”、“卤代(C3-C6)环烷基”、“卤代(C3-C6)环烷氧基”、“卤代(C1-C6)烷氧基”、“卤代(C2-C6)链烯基氧基”、“卤代(C2-C6)炔基氧基”、“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)链烯基硫基”、“卤代(C2-C6)炔基硫基”、“卤代(C2-C6)链烯基亚磺酰基”、“卤代(C2-C6)炔基亚磺酰基”、“卤代(C2-C6)链烯基磺酰基”、“卤代(C2-C6)炔基磺酰基”、“卤代(C3-C6)环烷硫基”、“卤代(C3-C6)环烷基亚磺酰基”、“卤代(C3-C6)环烷基磺酰基”、“卤代(C1-C6)烷氧基羰基氧基”、“卤代二(C1-C6)烷基氨基”或“(C1-C6)烷基羰基硫基”。
“(C1-C6)”、“(C2-C6)”、“(C3-C6)”等表述表示各种取代基的碳原子数的范围。此外,对于连接上述取代基而成的基团,也可以表示上述定义,例如,在“(C1-C6)烷氧基(C1-C6)烷基”的情况下,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(I)所示的稠杂环化合物的盐类,可以例示例如盐酸盐、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;与钠离子、钾离子、钙离子、三甲基铵根离子等无机或有机碱的盐类。
本发明的通式(I)所示的稠杂环化合物及其盐类有时在其结构式中具有1个或多个不对称中心,也有时存在两种以上的光学异构体和非对映异构体,本发明包含全部各光学异构体以及以任意的比例含有这些异构体的混合物。另外,本发明的通式(I)所示的化合物及其盐类也有时在其结构式中存在来源于碳-碳双键的两种几何异构体,本发明包含全部各几何异构体以及以任意的比例含有这些异构体的混合物。
在本发明的一个方式中,通式(I)所示的稠杂环化合物及其盐类优选为如下的稠杂环化合物及其盐类:
R1为(C1-C6)烷基;(C3-C6)环烷基;(C2-C6)链烯基;(C2-C6)炔基;卤代(C1-C6)烷基;(C1-C6)烷氧基(C1-C6)烷基;(C3-C6)环烷基(C1-C6)烷基;(C1-C6)烷硫基(C1-C6)烷基;(C1-C6)烷基亚磺酰基(C1-C6)烷基;(C1-C6)烷基磺酰基(C1-C6)烷基;氰基(C1-C6)烷基;(C1-C6)烷氧基羰基氧基(C1-C6)烷基;二(C1-C6)烷基氨基(C1-C6)烷基(二(C1-C6)烷基氨基的烷基可以相同或不同);苯基(C1-C6)烷基;或在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为卤素原子;(C1-C6)烷基;(C3-C6)环烷基;(C2-C6)链烯基;(C2-C6)炔基;卤代(C1-C6)烷基;(C1-C6)烷硫基;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;氢原子;(C1-C6)烷氧基;卤代(C1-C6)烷氧基;氨基;二(C1-C6)烷基氨基(二(C1-C6)烷基的烷基可以相同也可以不同);(C1-C6)烷基羰基氨基;(C1-C6)烷基磺酰基氨基;(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;(C1-C6)烷氧基羰基;或三(C1-C6)烷基甲硅烷基(C2-C6)炔基(三(C1-C6)烷基甲硅烷基的烷基可以相同也可以不同);
R3为氢原子;
R4为卤素原子;(C1-C6)烷基;卤代(C1-C6)烷基;巯基;(C1-C6)烷硫基;(C1-C6)烷基羰基硫基;卤代(C1-C6)烷硫基;在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或(C1-C6)烷基磺酰基;
R5为(C1-C6)烷基;(C3-C6)环烷基;卤代(C1-C6)烷基;(C1-C6)烷氧基(C1-C6)烷基;氨基;或(C1-C6)烷氧基;
A1、A2和A3可以相同或不同,为氮原子或C-R6基(在此,R6为(f1)氢原子),
m为0、1或2。
在本发明的一个方式中,通式(I)所示的稠杂环化合物及其盐类进一步优选为如下的稠杂环化合物及其盐类:
R1为(C1-C6)烷基;(C3-C6)环烷基;(C2-C6)链烯基;卤代(C1-C6)烷基;(C3-C6)环烷基(C1-C6)烷基;(C1-C6)烷硫基(C1-C6)烷基;氰基(C1-C6)烷基;(C1-C6)烷氧基羰基氧基(C1-C6)烷基;二(C1-C6)烷基氨基(C1-C6)烷基(二(C1-C6)烷基氨基的烷基可以相同或不同);或在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为卤素原子;(C1-C6)烷基;(C3-C6)环烷基;(C2-C6)链烯基;(C2-C6)炔基;卤代(C1-C6)烷基;(C1-C6)烷硫基;卤代(C1-C6)烷硫基;氢原子;卤代(C1-C6)烷氧基;氨基;二(C1-C6)烷基氨基(二(C1-C6)烷基的烷基可以相同也可以不同);(C1-C6)烷基羰基氨基;(C1-C6)烷基磺酰基氨基;(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;(C1-C6)烷氧基羰基;或三(C1-C6)烷基甲硅烷基(C2-C6)炔基(三(C1-C6)烷基甲硅烷基的烷基可以相同也可以不同);
R3为氢原子;
R4为卤素原子;卤代(C1-C6)烷基;巯基;(C1-C6)烷硫基;(C1-C6)烷基羰基硫基;卤代(C1-C6)烷硫基;在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或(C1-C6)烷基磺酰基;
R5为(C1-C6)烷基;(C3-C6)环烷基;或(C1-C6)烷氧基(C1-C6)烷基;
A1、A2和A3可以相同或不同,为氮原子或C-R6基(在此,R6为(f1)氢原子),
m为0、1或2。
本发明的稠杂环化合物或其盐类例如可以通过下述制造方法来制造,但本发明并不限定于此。
制造方法1
{式中,R1、R2、R3、R4、R5、A1、A2、A3和m与上述相同,X表示卤素原子}
步骤[a]的制造方法
使通式(2)所示的羧酸酰胺与通式(3)所示的化合物在金属催化剂、碱和惰性溶剂的存在下进行反应,由此能够制造通式(I-3)所示的羧酸酰胺化合物。本反应可以按照文献记载的方法(Org.Synth.78:23,;Coll.Vol.10:423、J.A.C.S.(1999),121(18),4369-4378)进行。
作为本发明中可以使用的金属催化剂,可以列举[1,1’-双(二苯基膦)二茂铁]二氯化钯(II)、[1,1’-双(二苯基膦)丙烷]二氯化钯(II)、[1,1’-双(二苯基膦)丁烷]二氯化钯(II)、双(二亚苄基丙酮)钯(0)、三(二亚苄基丙酮)二钯(0)等0价的钯化合物、乙酸钯(II)、氯化钯(II)、双(乙腈)二氯化钯(II)、双(苯甲腈)二氯化钯(II)、烯丙基氯化钯(II)二聚物、环戊二烯基烯丙基钯(II)等公知的钯催化剂。另外,也可以根据需要使用其中的两种以上。本发明中的钯催化剂的使用量相对于通式(2)所示的化合物通常在约0.001倍摩尔~0.1倍摩尔的范围内适当选择即可。
作为本发明中可以使用的碱,可以列举氢氧化锂、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;甲醇钠、乙醇钠、叔丁醇钠、叔丁醇钾等醇盐等;氢化钠、氢化钾等金属氢化物类;吡啶、甲基吡啶、二甲基吡啶、三乙胺、三丁胺、二异丙基乙胺等有机碱等。作为碱的使用量,相对于通式(2)所示的化合物在0.5倍摩尔~5.0倍摩尔的范围内适当选择即可。
作为本反应中可以使用的惰性溶剂,只要不显著抑制本反应即可,可以列举例如甲醇、乙醇、丙醇、丁醇、2-丙醇等醇类;二乙醚、四氢呋喃、二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、四氯化碳等卤代烃类;氯苯、二氯苯等卤代芳香族烃类;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,这些惰性溶剂可以单独使用或两种以上混合使用。
本反应中的反应温度通常在约0℃至所使用的溶剂的沸点的范围内进行即可,反应时间根据反应规模、反应温度等而不固定,在几分钟~48小时的范围内适当选择即可。反应结束后,将目标物利用常规方法从含有该目标物的反应体系中分离即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。另外,也可以在不进行分离、纯化的情况下进行下一步骤。根据情况,也可以在本制造步骤中进行下一步骤所述的脱水缩合反应,并省略下一步骤。
步骤[b]的制造方法
通式(I-2)所示的稠杂环化合物可以通过使通式(I-3)所示的化合物在稠合剂、碱和惰性溶剂的存在下进行反应来制造。
作为本反应中使用的稠合剂,可以例示例如氰基磷酸二乙酯(DEPC)、羰基双咪唑(CDI)、1,3-双环己基碳二亚胺(DCC)、氯碳酸酯类、2-氯-1-甲基碘代吡啶等,其使用量相对于通式(I-2)所示的化合物从1倍摩尔~1.5倍摩尔的范围内适当选择来使用即可。
作为碱,可以列举例如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾等无机碱类;乙酸钠、乙酸钾等乙酸盐类;叔丁醇钾、甲醇钠、乙醇钠等碱金属醇盐类;三乙胺、二异丙基乙胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯等叔胺类;吡啶、二甲基氨基吡啶等含氮芳香族化合物等,其使用量相对于通式(I-2)所示的化合物通常在1倍摩尔~10倍摩尔的范围内使用。
作为本反应中使用的惰性溶剂,只要不显著抑制本反应的进行即可,可以例示例如苯、甲苯、二甲苯等芳香族烃类;二氯甲烷、氯仿、四氯化碳等卤代烃类;氯苯、二氯苯等卤代芳香族烃类;二乙醚、甲基叔丁基醚;二烷、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惰性溶剂,这些惰性溶剂可以单独使用或两种以上混合使用。
本反应为等摩尔反应,因此,将各反应剂以等摩尔使用即可,但也可以过量地使用任意一种反应剂。反应温度可以在室温至所使用的惰性溶剂的沸点的范围内进行,反应时间根据反应规模、反应温度而不固定,在几分钟~48小时的范围内进行即可。
反应结束后,利用常规方法从含有目标物的反应体系中分离目标物即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。
步骤[c]的制造方法
可以通过使通式(I-2)所示的稠杂环化合物与通式(4)所示的硫醇化合物在碱的存在下在惰性溶剂中进行反应来制造通式(I-1)所示的稠杂环化合物。
作为本反应中可以使用的碱,可以列举例如氢氧化钠、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、氢化钾等氢化碱金属;甲醇钠、乙醇钠、叔丁醇钾等醇盐类。碱的使用量相对于通式(I-2)所示的化合物通常在约1倍摩尔~5倍摩尔的范围内使用。另外,也可以使用市售的甲硫醇钠、乙硫醇钠,这种情况下,可以不使用化合物(4)。
作为本反应中可以使用的惰性溶剂,只要不显著抑制本反应即可,可以列举例如甲醇、乙醇、丙醇、丁醇、2-丙醇等醇类;二乙醚、四氢呋喃、二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、四氯化碳等卤代烃类;氯苯、二氯苯等卤代芳香族烃类;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,这些惰性溶剂可以单独使用或两种以上混合使用。
本反应中的反应温度通常在约0℃至所使用的溶剂的沸点的范围内进行即可,反应时间根据反应规模、反应温度等而不固定,在几分钟~48小时的范围内适当选择即可。通式(4)所示的化合物相对于通式(I-1)所示的稠杂环化合物通常在约1倍摩尔~5倍摩尔的范围内使用。另外,本反应也可以在例如氮气、氩气这样的不活泼气体的氛围下进行。反应结束后,利用常规方法从含有目标物的反应体系中分离目标物即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。
步骤[d]的制造方法
本反应中,可以通过使通式(I-1)所示的稠杂环化合物在惰性溶剂中与氧化剂进行反应来制造通式(I)所示的稠杂环化合物。作为本反应中使用的氧化剂,可以列举过氧化氢水溶液、过苯甲酸、间氯过苯甲酸等过氧化物等。这些氧化剂相对于通式(I-1)所示的稠杂环化合物类可以在0.8倍摩尔~5倍摩尔的范围内适当选择,优选1倍摩尔~2倍摩尔的范围。
作为本反应中可以使用的惰性溶剂,只要不显著抑制本反应即可,可以列举例如二乙醚、四氢呋喃、二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、四氯化碳等卤代烃类;氯苯、二氯苯等卤代芳香族烃类;乙腈等腈类;乙酸乙酯等酯类;甲酸、乙酸等有机酸类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、1,3-二甲基-2-咪唑啉酮、水等极性溶剂,这些惰性溶剂可以单独使用或两种以上混合使用。
本反应中的反应温度在-10℃至所使用的惰性溶剂的回流温度的范围内适当选择即可。反应时间根据反应规模、反应温度等而变化,并不固定,在几分钟~48小时的范围内适当选择即可。反应结束后,利用常规方法从含有目标物的反应体系中分离目标物即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。
本发明的原料物质或中间体例如可以通过以下的方法来制造。
中间体制造方法
[式中,R3、R4和R5与上述含义相同,X表示卤素原子]
通式(3)可以通过以下的方法来制造。
步骤[e]的制造方法
通式(3-1)所示的化合物可以通过在惰性溶剂中使通式(3-2)所示的化合物与通式(5)所示的氨基化合物进行反应来制造。氨基化合物(5)相对于化合物(3-2)可以在1倍摩尔~5倍摩尔的范围内适当选择。
作为本反应中使用的惰性溶剂,只要不显著抑制本反应的进行即可,可以例示例如苯、甲苯、二甲苯等芳香族烃类;二氯甲烷、氯仿、四氯化碳等卤代烃类;氯苯、二氯苯等卤代芳香族烃类;二乙醚、甲基叔丁基醚、二烷、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-咪唑啉酮等惰性溶剂,这些惰性溶剂可以单独使用或两种以上混合使用。
可以根据需要使用碱,作为碱,可以列举例如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾等无机碱类;乙酸钠、乙酸钾等乙酸盐类;叔丁醇钾、甲醇钠、乙醇钠等碱金属醇盐类;三乙胺、二异丙基乙胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯等叔胺类;吡啶、二甲基氨基吡啶等含氮芳香族化合物等,其使用量相对于通式(3-1)所示的化合物通常在1倍摩尔~10倍摩尔的范围内使用。
本反应中的反应温度在-10℃至所使用的惰性溶剂的回流温度的范围内适当选择即可。反应时间根据反应规模、反应温度等而变化,并不固定,在几分钟~48小时的范围适当选择即可。
反应结束后,利用常规方法从含有目标物的反应体系中分离目标物即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。
步骤[f]的制造方法
通式(3)所示的化合物可以通过在惰性溶剂中使通式(3-1)所示的化合物与卤化剂进行反应来制造。
作为本反应中可以使用的惰性溶剂,只要不显著抑制本反应即可,可以列举例如甲醇、乙醇、丙醇、丁醇、2-丙醇等醇类;二乙醚、四氢呋喃、二烷等链状或环状醚类;苯、甲苯、二甲苯等芳香族烃类;乙酸乙酯等酯类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、1,3-二甲基-2-咪唑啉酮、水、乙酸等极性溶剂,这些惰性溶剂可以单独使用或两种以上混合使用。
作为反应中使用的卤化剂,可以列举例如氟、氯、溴、碘等卤素分子;NCS、NBS等卤代琥珀酰亚胺类;DIH等卤代乙内酰脲类;亚硫酰氯等。
本反应中的反应温度在-30℃至所使用的惰性溶剂的回流温度的范围内适当选择即可。反应时间根据反应规模、反应温度等而变化,并不固定,在几分钟~48小时的范围内适当选择即可。
反应结束后,利用常规方法从含有目标物的反应体系中分离目标物即可,可以根据需要通过利用再结晶、柱层析等进行纯化来制造目标物。
接着,下面示出本发明化合物的具体例。在下述的表中,Me表示甲基,Et表示乙基,n-Pr表示正丙基,i-Pr表示异丙基,c-Pr表示环丙基,Ac表示乙酰基,t-Bu表示叔丁基,Allyl表示烯丙基,Propargyl表示炔丙基(2-丙炔基),c-Bu表示环丁基,c-Pent表示环戊基,c-Hex表示环己基,Ph表示苯基,Bn表示苄基。物性表示熔点(℃)、折射率nD(测定温度:℃)或NMR。
[表1]
第1表
需要说明的是,在第1表的化合物中,R3=H、A1和A2=CH。
[表2]
续第1表
第1表的化合物中,R3=H、A1和A2=CH。
[表3]
续第1表
第1表的化合物中,R3=H、A1和A2=CH。
[表4]
NMR数据
[表5]
第2表
第2表的化合物中,R3=H、A1和A2=CH。
[表6]
第3表
第3表的化合物中,R3=H、A1和A2=CH。
[表7]
续第3表
第3表的化合物中,R3=H、A1和A2=CH。
[表8]
续第3表
第3表的化合物中,R3=H、A1和A2=CH。
[表9]
第4表
第4表的化合物中,R3=H、A1和A2=CH。
[表10]
续第4表
第4表的化合物中,R3=H、A1和A2=CH。
[表11]
第5表
第5表的化合物中,R3=H、A1和A2=CH。
[表12]
第6表
第6表的化合物中,R3=H、A1和A2=CH。
[表13]
第7表
第7表的化合物中,R3=H、A1和A2=CH。
[表14]
续第7表
第7表的化合物中,R3=H、A1和A2=CH。
含有本发明的通式(I)所示的稠杂环化合物或其盐类作为有效成分的农业园艺用杀虫剂适合于防除危害水稻、果树、蔬菜、其他作物和花卉类的各种农林、园艺、储粮害虫、卫生害虫或者线虫类等害虫。
作为上述害虫或线虫类等,可以例示以下的害虫或线虫。
作为鳞翅目(Lepidoptera)害虫,可以列举例如褐边绿刺蛾(Parasa consocia)、桥夜蛾(Anomis mesogona)、柑橘凤蝶(Papilio xuthus)、日豆小卷蛾(Matsumuraesesazukivora)、肩杆野螟(Ostrinia scapulalis)、非洲粘虫(Spodoptera exempta)、美国白蛾(Hyphantria cunea)、亚洲玉米螟(Ostrinia furnacalis)、粘虫(Pseudaletiaseparata)、衣蛾(Tinea translucens)、糠麸尖翅小卷蛾(Bactra furfurana)、直纹稻弄蝶(Parnara guttata)、稻显纹刷须野螟(Marasmia exigua)、直纹稻弄蝶(Parnaraguttata)、稻蛀茎夜蛾(Sesamia inferens)、三环甘薯麦蛾(Brachmia triannulella)、黄刺蛾(Monema flavescens)、粉纹夜蛾(Trichoplusia ni)、豆肋膜野螟(Pleuroptyaruralis)、小蜻蜓尺蛾(Cystidia couaggaria)、亮灰蝶(Lampides boeticus)、咖啡透翅天蛾(Cephonodes hylas)、棉铃虫(Helicoverpa armigera)、曼栎蚕舟蛾(Phalerodontamanleyi)、大避债蛾(Eumeta japonica)、欧洲粉蝶(Pieris brassicae)、黄褐天幕毛虫(Malacosoma neustria testacea)、柿举肢蛾(Stathmopoda masinissa)、柿细蛾(Cuphodes diospyrosella)、角纹卷叶虫(Archips xylosteanus)、黄地老虎(Agrotissegetum)、甘薯小卷蛾(Tetramoera schistaceana)、黄凤蝶北亚亚种(Papilio machaonhippocrates)、黄斑蝙蝠蛾(Endoclyta sinensis)、银纹潜蛾(Lyonetia prunifoliella)、金纹小潜细蛾(Phyllonorycter ringoneella)、栗白小卷蛾(Cydia kurokoi)、栗绿小卷蛾(Eucoenogenes aestuosa)、鲜食葡萄小卷蛾(Lobesia botrana)、中国绿刺蛾(Latoiasinica)、巴塘暗斑螟(Euzophera batangensis)、中华箭头细卷蛾(Phalonidiamesotypa)、桑斑雪灯蛾(Spilosoma imparilis)、桑绢野螟(Glyphodes pyloalis)、桑卷叶蛾(Olethreutes mori)、幕谷蛾(Tineola bisselliella)、蝙蝠蛾(Endoclytaexcrescens)、谷蛾(Nemapogon granellus)、苹果透翅蛾(Synanthedon hector)、苹果皮小卷蛾(Cydia pomonella)、小菜蛾(Plutella xylostella)、稻纵卷叶野螟(Cnaphalocrocismedinalis)、蛀茎夜蛾(Sesamia calamistis)、三化螟(Scirpophaga incertulas)、蓝草螟蛾(Pediasia teterrellus)、马铃薯麦蛾(Phthorimaea operculella)、蚁舟蛾(Stauropusfagi persimilis)、豆荚斑螟(Etiella zinckenella)、贪夜蛾(Spodoptera exigua)、白斑蝙蝠蛾(Palpifer sexnotata)、灰翅夜蛾(Spodoptera mauritia)、稻白螟(Scirpophagainnotata)、八字地老虎(Xestia c-nigrum)、淡贪夜蛾(Spodoptera depravata)、地中海粉斑螟(Ephestia kuehniella)、李尺蛾(Angerona prunaria)、分月扇舟蛾(Closteraanastomosis)、
大豆尺夜蛾(Pseudoplusia includens)、川豆小卷蛾(Matsumuraeses falcana)、烟实夜蛾(Helicoverpa assulta)、黑点丫纹夜蛾(Autographa nigrisigna)、小地老虎(Agrotis ipsilon)、茶黄毒蛾(Euproctis pseudoconspersa)、棉褐带卷蛾(Adoxophyesorana)、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(Clostera anachoreta)、苜蓿夜蛾(Heliothis maritima)、葡萄长须卷蛾(Sparganothis pilleriana)、玉米干夜蛾(Busseola fusca)、亚折带黄毒蛾(Euproctis subflava)、大鹰尺蛾(Biston robustum)、美洲棉铃虫(Heliothis zea)、烦夜蛾(Aedia leucomelas)、梨娜刺蛾(Narosoideusflavidorsalis)、梨剑纹夜蛾(Viminia rumicis)、梨潜蛾(Bucculatrix pyrivorella)、梨小食心虫(Grapholita molesta)、梨潜皮细蛾(Spulerina astaurota)、梨云翅斑螟(Ectomyelois pyrivorella)、二化螟(Chilo suppressalis)、葱潜叶蛾(Acrolepiopsissapporensis)、印度谷斑螟(Plodia interpunctella)、菜心野螟(Hellula undalis)、麦蛾(Sitotroga cerealella)、斜纹贪夜蛾(Spodoptera litura)、绿豆芽蛾(Eucosmaaporema)、草莓长翅卷蛾(Acleris comariana)、球须刺蛾(Scopelodes contractus)、旋古毒蛾(Orgyia thyellina)、草地夜蛾(Spodoptera frugiperda)、扎氏秆野螟(Ostriniazaguliaevi)、稻螟蛉夜蛾(Naranga aenescens)、三线茶蚕蛾(Andraca bipunctata)、葡萄透翅蛾(Paranthrene regalis)、缺角天蛾(Acosmeryx castanea)、葡萄潜叶蛾(Phyllocnistis toparcha)、葡萄浆果小卷蛾(Endopiza viteana)、环针单纹蛾(Eupoecillia ambiguella)、大豆夜蛾(Anticarsia gemmatalis)、烟草云卷蛾(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)、大豆花细蛾(Caloptilia soyella)、柑橘叶潜蛾(Phyllocnistis citrella)、豆褐啮叶野螟(Omiodes indicata)、杏黄卷蛾(Archipsfuscocupreanus)、银纹夜蛾(Acanthoplusia agnata)、桑蓑蛾(Bambalina sp.)、桃蛀果蛾(Carposina niponensis)、桃蛀野螟(Conogethes punctiferalis)、透翅蛾属(Synanthedon sp.)、桃潜叶蛾(Lyonetia clerkella)、玉斑凤蝶(Papilio helenus)、东方豆粉蝶(Colias erate poliographus)、苹掌舟蛾(Phalera flavescens)、菜粉蝶日本亚种(Pieris rapae crucivora)、菜粉蝶(Pieris rapae)等粉蝶属、盗毒蛾(Euproctissimilis)、铃木潜叶蛾(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)、草图卷蛾(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)、芽白小卷蛾(Spilonota lechriaspis)、梨叶斑蛾(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)和鼎点金刚钻(Earias cupreoviridis)等。
作为半翅目(Hemiptera)害虫,可以列举例如花角绿蝽(Nezara antennata)、高粱红带盲蝽(Stenotus rubrovittatus)、黑条红蝽象(Graphosoma rubrolineatum)、稻叶赤须盲蝽(Trigonotylus coelestialium)等、班姬缘蝽(Aeschynteles maculatus)、苍白肉盲蝽(Creontiades pallidifer)、棉红蝽(Dysdercus cingulatus)、黑褐圆盾蚧(Chrysomphalus ficus)、红肾圆盾蚧(Aonidiella aurantii)、大褐蜩(Graptopsaltrianigrofuscata)、谷长蝽(Blissusleucopterus)、吹棉蚧(Icerya purchasi)、海壁蝽(Piezodorus hybneri)、长稻褐蝽(Lagynotomus elongatus)、黄稻白翅叶蝉(Thaiasubrufa)、稻黑蝽(Scotinophara lurida)、月季蚜(Sitobion ibarae)、岩崎蝽象(Stariodes iwasakii)、椰圆盾蚧(Aspidiotus destructor)、白苔盲蝽(Taylorilyguspallidulus)、杏瘤蚜(Myzusmumecola)、李白盾蚧(Pseudaulacaspis prunicola)、豌豆蚜(Acyrthosiphon pisum)、纹须同缘蝽(Anacanthocoris striicornis)、日本庭园盲蝽(Ectometopterus micantulus)、日本二星蝽(Eysarcoris lewisi)、叶足缘蝽(Molipteryxfuliginosa)、大青叶蝉(Cicadella viridis)、红腹缢管蚜(Rhopalosophumrufiabdominalis)、橄榄黑盔蚧(Saissetia oleae)、温室粉虱(Trialeurodesvaporariorum)、栎辜小叶蝉(Aguriahana quercus)、草盲蝽属(Lygus spp.)、桦棉斑蚜(Euceraphis punctipennis)、柞安盾蚧(Andaspis kashicola)、橘软蜡蚧(Coccuspseudomagnoliarum)、甘蔗异背长蝽(Cavelerius saccharivorus)、菊贝脊网蝽(Galeatusspinifrons)、菊小长管蚜(Macrosiphoniella sanborni)、黄肾圆盾蚧(Aonidiellacitrina)、混茶翅蝽(Halyomorpha mista)、一斑冠网蝽(Stephanitis fasciicarina)、樟个木虱(Trioza camphorae)、中稻缘蝽(Leptocorisa chinensis)、栎个木虱(Triozaquercicola)、黄角肩网蝽(Uhlerites latius)、葡萄伴斑叶蝉(Erythroneura comes)、细长蝽(Paromius exiguus)、柘榴重圆盾蚧(Duplaspidiotus claviger)、二条黑尾叶蝉(Nephotettix nigropictus)、东方庭园盲蝽(Halticiellus insularis)、甘蔗角扁飞虱(Perkinsiella saccharicida)、苹果木虱(Psylla malivorella)、桑木虱(Anomomeuramori)、康氏粉蚧(Pseudococcus longispinis)、桑白盾蚧(Pseudaulacaspis pentagona)、桑树棉蚧(Pulvinaria kuwacola)、绿盲蝽(Apolygus lucorum)、短翅球胸长蝽(Togohemipterus)、橘声蚜(Toxoptera aurantii)、
糖粉蚧(Saccharicoccus sacchari)、蔗根蚜(Geoica lucifuga)、瓶额飞虱(Numata muiri)、圣琼斯康盾蚧(Comstockaspis perniciosa)、柑橘尖盾蚧(Unaspiscitri)、土豆沟无网蚜(Aulacorthum solani)、广二星蝽(Eysarcoris ventralis)、银叶粉虱(Bemisia argentifolii)、稻大白叶蝉(Cicadella spectra)、常春藤圆盾蚧(Aspidiotus hederae)、粟缘蝽(Liorhyssus hyalinus)、黑背小木虱(Calophyanigridorsalis)、白背飞虱(Sogatella furcifera)、瘤突修尾蚜(Megoura crassicauda)、甘蓝蚜(Brevicoryne brassicae)、大豆蚜(Aphis glycines)、大稻缘蝽(Leptocorisaoratorius)、二点黑尾叶蝉(Nephotettix virescens)、莴苣指管蚜(Uroeuconformosanum)、烟草盲蝽(Cyrtopeltis tennuis)、甘薯粉虱(Bemisia tabaci)、欧洲桃球蚧(Lecanium persicae)、茶片盾蚧(Parlatoria theae)、牡丹网盾蚧(Pseudaonidiapaeoniae)、大贯小绿叶蝉(Empoasca onukii)、斯氏珀蝽(Plautia stali)、百合西圆尾蚜(Dysaphis tulipae)、马铃薯长管蚜(Macrosiphum euphorbiae)、拟梨冠网蝽(Stephanitis pyrioides)、角蜡蚧(Ceroplastes ceriferus)、山茶片盾阶(Parlatoriacamelliae)、后丽盲蝽(Apolygus spinolai)、黑尾叶蝉(Nephotettix cincticeps)、光缘青蝽(Glaucias subpunctatus)、藜杂毛盲蝽(Orthotylus flavosparsus)、玉米缢管蚜(Rhopalosiphum maidis)、ト玉米花翅飞虱(Peregrinus maidis)、尖角二星蝽(Eysarcorisparvus)、温带臭虫(Cimex lectularius)、椴松木虱(Psylla abieti)、褐飞虱(Nilaparvata lugens)、烟木虱(Psylla tobirae)、
皱纹菜蝽(Eurydema rugosum)、梨二叉蚜(Schizaphis piricola)、梨黄木虱(Psylla pyricola)、梨星片盾蚧(Parlatoreopsis pyri)、梨冠网蝽(Stephanitisnashi)、紫藤灰粉蚧(Dysmicoccus wistariae)、梨蚧(Lepholeucaspis japonica)、梨园尾蚜(Sappaphis piri)、萝卜蚜(Lipaphis erysimi)、葱新弓翅蚜(Neotoxopteraformosana)、莲缢管蚜(Rhopalosophum nymphaeae)、蔷薇埃小叶蝉(Edwardsianarosae)、百合并盾蚧(Pinnaspisaspidistrae)、赤杨木虱(Psylla alni)、叶蝉(Speusotettixsubfusculus)、杂食性叶蝉(Alnetoidia alneti)、黍白背飞虱(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(Uhlerites debile)、灰飞虱(Laodelphaxstriatella)、河北菜蝽(Eurydema pulchrum)、长肩棘缘蝽(Cletus trigonus)、刻点铲头沫蝉(Clovia punctata)、小绿叶蝉属(Empoasca spp.)、广食褐软蚧(Coccushesperidum)、莎草鼓胸长蝽(Pachybrachius luridus)、藤臀纹粉蚧(Planococcuskraunhiae)、梯牧草二斑盲蝽(Stenotus binotatus)、葡萄叶蝉(Arboridia apicalis)、二点叶蝉(Macrosteles fascifrons)、斑须蝽(Dolycoris baccarum)、三环苜蝽(Adelphocoris triannulatus)、葡萄根瘤蚜(Viteus vitifolii)、樱桃瘤缘蝽(Acanthocoris sordidus)、大稻缘蝽(Leptocorisa acuta)、竹类巨股长蝽(Macropesobnubilus)、稻棘缘蝽(Cletus punctiger)、豆蜂缘蝽(Riptortus clavatus)、马铃薯木虱(Paratrioza cockerelli)、
柳肋尖胸沫蝉(Aphrophora costalis)、日本草盲蝽(Lygus disponsi)、东亚草盲蝽(Lygus saundersi)、松树皑粉蚧(Crisicoccus pini)、松小叶蝉(Empoasca abietis)、核桃皑粉蚧(Crisicoccus matsumotoi)、豆蚜(Aphis craccivora)、臭蝽(Megacoptapunctatissimum)、二星蝽(Eysarcoris guttiger)、紫牡蛎盾蚧(Lepidosaphes beckii)、柑桔木虱(Diaphorina citri)、褐橘声蚜(Toxoptera citricidus)、橘臀纹粉蚧(Planococcus citri)、柑橘粉虱(Dialeurodes citri)、橘刺粉虱(Aleurocanthusspiniferus)、橘小粉蚧(Pseudococcus citriculus)、小桔塔叶蝉(Zyginella citri)、橘小棉蚧(Pulvinaria citricola)、番木瓜软蚧(Coccus discrepans)、樟网盾蚧(Pseudaonidia duplex)、橘棉蚧(Pulvinaria aurantii)、东方球蜡蚧(Lecanium corni)、稻绿蝽(Nezara viridula)、二刺狭盲蝽(Stenodema calcaratum)、禾谷缢管蚜(Rhopalosiphum padi)、玉米缢管蚜(Sitobion akebiae)、麦二叉蚜(Schizaphisgraminum)、麦绿草叶蝉(Sorhoanus tritici)、李短尾蚜(Brachycaudus helichrysi)、紫翅果蝽(Carpocoris purpureipennis)、桃蚜(Myzus persicae)、梅大尾蚜(Hyalopteruspruni)、柳蚜(Aphis farinose yanagicola)、柳后燧网蝽(Metasalis populi)、矢尖盾蚧(Unaspis yanonensis)、芙蓉木虱(Mesohomotoma camphorae)、异绣线菊蚜(Aphisspiraecola)、苹果蚜(Aphis pomi)、榆蛎盾蚧(Lepidosaphes ulmi)、苹木虱(Psyllamali)、黄足苹盲蝽(Heterocordylus flavipes)、苹果瘤蚜(Myzus malisuctus)、苹果蚜虫(Aphidonuguis mali)、苹斑叶蝉(Orientus ishidai)、苹果蚜(Ovatus malicolens)、苹果棉蚜(Eriosoma lanigerum)、红龟蜡蚧(Ceroplastes rubens)和棉蚜(Aphis gossypii)等。
作为鞘翅目(Coleoptera)害虫,可以列举例如合欢双条天牛(Xystroceraglobosa)、毒隐翅虫(Paederus fuscipes)、金边青花金龟(Eucetonia roelofsi)、绿豆象(Callosobruchus chinensis)、甘薯象(Cylas formicarius)、紫苜蓿叶象(Hyperapostica)、稻象(Echinocnemus squameus)、水稻负泥虫(Oulema oryzae)、长腿水叶甲(Donacia provosti)、稻水象(Lissorhoptrus oryzophilus)、甘薯叶甲(Colasposomadauricum)、西印度甘薯象(Euscepes postfasciatus)、墨西哥豆瓢虫(Epilachnavarivestis)、菜豆象(Acanthoscelides obtectus)、玉米根叶甲(Diabrotica virgiferavirgifera)、李蓝卷象(Involvulus cupreus)、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)、黄星桑天牛(Psacothea hilaris)、黄斑天牛(Aeolesthes chrysothrix)、蒙栎象(Curculiosikkimensis)、黄斑露尾甲(Carpophilus hemipterus)、小青花金龟(Oxycetoniajucunda)、根萤叶甲属(Diabrotica spp.)、华绿彩丽金龟(Mimela splendens)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium castaneum)、米象(Sitophilus oryzae)、亚扁粉盗(Palorus subdepressus)、日本鳃金龟(Melolontha japonica)、白斑星天牛(Anoplophora malasiaca)、大点拟粉虫(Neatus picipes)、马铃薯叶甲(Leptinotarsadecemlineata)、黄瓜十一星叶甲(Diabrotica undecimpunctata howardi)、结缕草象甲(Sphenophorus venatus)、十四点负泥虫(Crioceris quatuordecimpunctata)、梅球颈象(Conotrachelus nenuphar)、
大根缘象虫(Ceuthorhynchidius albosuturalis)、小猿叶甲(Phaedonbrassicae)、烟草窃蠹(Lasioderma serricorne)、日本根瘤象(Sitona japonicus)、斑喙丽金龟(Adoretus tenuimaculatus)、黄粉甲(Tenebrio molitor)、具角胸叶甲(Basileptabalyi)、小三叶草叶象(Hypera nigrirostris)、蓼凹胫跳甲(Chaetocnema concinna)、古铜异丽金龟(Anomala cuprea)、沥青七鳃金龟(Heptophylla picea)、茄二十八星瓢虫(Epilachna vigintioctopunctata)、长角叶甲(Diabrotica longicornis)、花金龟(Eucetonia pilifera)、叩甲属(Agriotes spp.)、黑毛皮蠹(Attagenus unicolorjaponicus)、斑鞘豆叶甲(Pagria signata)、多色异丽金龟(Anomala rufocuprea)、姬拟粉盗(Palorus ratzeburgii)、小粉虫(Alphitobius laevigatus)、小圆皮蠹(Anthrenusverbasci)、褐粉蠹(Lyctus brunneus)、杂拟谷盗(Tribolium confusum)、黑条麦萤叶甲(Medythia nigrobilineata)、葡萄脊虎天牛(Xylotrechus pyrrhoderus)、美国马铃薯跳甲(Epitrix cucumeris)、纵坑切梢小蠹(Tomicus piniperda)、松墨天牛(Monochamusalternatus)、日本弧丽金龟(Popillia japonica)、豆芫菁(Epicauta gorhami)、玉米象(Sitophilus zeamais)、日本草虎象(Rhynchites heros)、蔬菜象(Listroderescostirostris)、四纹豆象(Callosobruchus maculatus)、苹霜绿树叶象(Phyllobiusarmatus)、苹花象(Anthonomus pomorum)、铜绿里叶甲(Linaeidea aenea)和棉铃象(Anthonomus grandis)等。
作为双翅目(Diptera)害虫,可以列举例如淡色库蚊(Culex pipiens pallens)、菠菜泉蝇(Pegomya hyoscyami)、南美斑潜蝇(Liriomyza huidobrensis)、家蝇(Muscadomestica)、稻杆蝇(Chlorops oryzae)、イネクキ稻毛眼水蝇(Hydrellia sasakii)、日本稻潜蝇(Agromyza oryzae)、大麦毛眼水蝇(Hydrellia griseola)、麦叶毛眼水蝇(Hydrellia griseola)、菜豆蛇潜蝇(Ophiomyia phaseoli)、瓜寡鬃实蝇(Dacuscucurbitae)、樱桃果蝇(Drosophila suzukii)、日本辣实蝇(Rhacochlaena japonica)、厩腐蝇(Muscina stabulans)、东亚异蚤蝇(Megaselia spiracularis)等蚤蝇属、毛蠓(Clogmia albipunctata)、稻大蚊(Tipula aino)、伏蝇(Phormia regina)、三带喙库蚊(Culex tritaeniorhynchus)、中华按蚊(Anopheles sinensis)、甘蓝种蝇(Hylemyabrassicae)、大豆荚瘿蝇(Asphondylia sp.)、灰地种蝇(Delia platura)、葱地种蝇(Deliaantiqua)、樱桃绕实蝇(Rhagoletis cerasi)、骚扰库蚊(Culex pipiens molestusForskal)、地中海实蝇(Ceratitis capitata)、库拓果实蝇(Bradysia agrestis)、肖藜泉蝇(Pegomya cunicularia)、蔬菜斑潜蝇(Liriomyza sativae)、瓜斑潜蝇(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)、三叶草斑潜蝇(Liriomyza trifolii)、蔬菜斑潜蝇(Liriomyza sativae)、橘果实蝇(Dacus dorsalis)、橘园寡鬃实蝇(Dacus tsuneonis)、麦红吸浆虫(Sitodiplosismosellana)、黑腹麦秆蝇(Meromuza nigriventris)、墨西哥按实蝇(Anastrepha ludens)和苹果实蝇(Rhagoletis pomonella)等。
作为膜翅目(Hymenoptera)害虫,可以列举例如双针蚁(Pristomyrmex pungens)、肿腿蜂类、厨蚁(Monomorium pharaonis)、宽节大头蚁(Pheidole noda)、菜叶蜂(Athaliarosae)、栗瘿蜂(Dryocosmus kuriphilus)、黑蚁(Formica fusca japonica)、大黄蜂类、黄尾大黄蜂(Athalia infumata infumata)、玫瑰三节叶蜂(Arge pagana)、日本菜叶蜂(Athalia japonica)、切叶蚁(Acromyrmex spp.)、火蚁属(Solenopsis spp.)、苹果三节叶蜂(Arge mali)和无毛凹臭蚁(Ochetellus glaber)等。
作为直翅目(Orthoptera)害虫,可以列举例如尖头草螽(Homorocoryphuslineosus)、蝼蛄属(Gryllotalpa sp.)、小稻蝗(Oxya hyla intricata)、北海道稻蝗(Oxyayezoensis)、亚洲飞蝗(Locusta migratoria)、日本稻蝗(Oxya japonica)、稻螽(Homorocoryphus jezoensis)和北京油葫芦(Teleogryllus emma)等。
作为缨翅目(Thysanoptera)害虫,可以列举例如红带月蓟马(Selenothripsrubrocinctus)、稻蓟马(Stenchaetothrips biformis)、稻单管蓟马(Haplothripsaculeatus)、柿管蓟马(Ponticulothrips diospyrosi)、黄蓟马(Thrips flavus)、玉米黄呆蓟马(Anaphothrips obscurus)、樟管滑蓟马(Liothrips floridensis)、唐菖蒲简蓟马(Thrips simplex)、莉黑毛蓟马(Thrips nigropilosus)、温室蓟马(Heliothripshaemorrhoidalis)、伪棍桑蓟马(Pseudodendrothrips mori)、菊小头蓟马(Microcephalothrips abdominalis)、栲树皮蓟马(Leeuwenia pasanii)、栲树率值皮蓟马(Litotetothrips pasaniae)、柑橘硬蓟马(Scirtothrips citri)、中华单管蓟马(Haplothrips chinensis)、大豆奇菌蓟马(Mycterothrips glycines)、粗毛蓟马(Thripssetosus)、茶黄硬蓟马(Scirtothrips dorsalis)、米氏棍蓟马(Dendrothrips minowai)、黑单管蓟马(Haplothrips niger)、烟蓟马(Thrips tabaci)、葱蓟马(Thrips alliorum)、黄胸蓟马(Thrips hawaiiensis)、库氏单管蓟马(Haplothrips kurdjumovi)、袖指蓟马(Chirothrips manicatus)、丽花蓟马(Frankliniella intonsa)、色蓟马(Thripscoloratus)、西花蓟马(Franklinella occidentalis)、棕榈蓟马(Thrips palmi)、百合花蓟马(Frankliniella lilivora)和百合鳞茎滑蓟马(Liothrips vaneeckei)等。
作为蜱螨目(acari)害虫,可以列举例如红纤恙螨(Leptotrombidium akamushi)、卢氏叶螨(Tetranychus ludeni)、变异革蜱(Dermacentor variabilis)、截形叶螨(Tetranychus truncatus)、柏氏禽刺螨(Ornithonyssus bacoti)、犬蠕形螨(Demodexcanis)、山楂叶螨(Tetranychus viennensis)、神泽氏叶螨(Tetranychus kanzawai)、血红扇头蜱(Rhipicephalus sanguineus)等蜱类、马六甲肉食螨(Cheyletus malaccensis)、腐食酪螨(Tyrophagus putrescentiae)、粉尘螨(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)、林禽刺螨(Ornithonyssus sylvairum)、二斑叶螨(Tetranychus urticae)、中国瘿螨(Eriophyes chibaensis)、葡萄短须螨(Brevipalpus sp.)、人疥螨(Sarcoptesscabiei)、长角血蜱(Haemaphysalis longicornis)、肩突硬蜱(Ixodes scapularis)、似食酪螨(Tyrophagus similis)、普通肉食螨(Cheyletus eruditus)、柑橘全爪螨(Panonychuscitri)、莫氏肉食螨(Cheyletus moorei)、紫红短须螨(Brevipalpus phoenicis)、耳痒螨(Octodectes cynotis)、屋尘螨(Dermatophagoides ptrenyssnus)、褐黄血蜱(Haemaphysalis flava)、卵形硬蜱(Ixodes ovatus)、琉球柑橘锈螨(Phyllocoptrutacitri)、斯氏针刺瘿螨(Aculus schlechtendali)、苹果全爪螨(Panonychus ulmi)、美洲花蜱(Amblyomma americanum)和鸡皮刺螨(Dermanyssus gallinae)、罗宾根螨(Rhyzoglyphus robini)、根螨属(Sancassania sp.)等。
作为等翅目(Isoptera)害虫,可以列举例如漂胸散白蚁(Reticulitermesmiyatakei)、小楹白蚁(Incisitermes minor)、台湾乳白蚁(Coptotermes formosanus)、日本湿木蚁(Hodotermopsis japonica)、散白蚁属(Reticulitermes sp.)、黄肢散白蚁(Reticulitermes flaviceps amamianus)、串本白蚁(Glyptotermes kushimensis)、广州乳白蚁(Coptotermes guangzhoensis)、恒春新白蚁(Neotermes koshunensis)、儿玉白蚁(Glyptotermes kodamai)、赤树白蚁(Glyptotermes satsumensis)、截头堆砂白蚁(Cryptotermes domesticus)、黑翅土白蚁(Odontotermes formosanus)、中岛树白蚁(Glyptotermes nakajimai)、近扭白蚁(Pericapritermes nitobei)和黄胸散白蚁(Reticulitermes speratus)等。
作为蜚蠊目(blattodea)害虫,可以列举例如黑胸大蠊(Periplanetafuliginosa)、德国小蠊(Blattella germanica)、东方蜚蠊(Blatta orientalis)、褐斑大蠊(Periplaneta brunnea)、拟德国小蠊(Blattella lituricollis)、日本大蠊(Periplaneta japonica)和美洲大蠊(Periplaneta americana)等。
作为蚤目(Siphonaptera),可以列举例如人蚤(Pulex irritans)、猫蚤(Ctenocephalides felis)和鸡蚤(Ceratophyllus gallinae)等。
作为线虫类(nematodes),可以列举例如草莓芽线虫(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)、南方根结线虫(Meloidogyne incognita)、马铃薯金线虫(Globodera rostochiensis)、爪哇根结线虫(Meloidogyne javanica)、大豆异皮线虫(Heterodera glycines)、咖啡短体线虫(Pratylenchus coffeae)、落选短体线虫(Pratylenchus neglectus)和半穿刺线虫(Tylenchus semipenetrans)等。
作为软体动物类,可以列举例如福寿螺(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)和螺蛳(Acusta despecta sieboldiana)等。
另外,本发明的农业园艺用杀虫剂对于作为其他害虫的番茄斑潜蝇(Tutaabsoluta)也具有强杀虫效果。
另外,作为防除对象之一的动物寄生性的蜱螨,可以列举例如微小牛蜱(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)、衣亚斯血蜱(Haemaphysalis ias)、卵形硬蜱(Ixodes ovatus)、日本硬蜱(Ixodes nipponensis)、全沟硬蜱(Ixodes persulcatus)、龟形花蜱(Amblyomma testudinarium)、奥特盖血蜱(Haemaphysalis megaspinosa)、网状革蜱(Dermacentor reticulatus)和台湾革蜱(Dermacentor taiwanesis)之类的蜱类、鸡皮刺螨(Dermanyssus gallinae)、林禽刺螨(Ornithonyssus sylviarum)和囊禽刺螨(Ornithonyssus bursa)之类的禽螨类、威氏真恙螨(Eutrombicula wichmanni)、红纤恙螨(Leptotrombidium akamushi)、苍白纤恙螨(Leptotrombidium pallidum)、富士纤恙螨(Leptotrombidium fuji)、土佐恙螨(Leptotrombidium tosa)、秋收恙螨(Neotrombicula autumnalis)、北美恙螨(Eutrombicula alfreddugesi)和宫川恙螨(Helenicula miyagawai)之类的恙虫类、犬姬螯螨(Cheyletiella yasguri)、兔姬螯螨(Cheyletiella parasitivorax)和猫姬螯螨(Cheyletiella blakei)之类的肉食螨类、兔库螨(Psoroptes cuniculi)、牛足螨(Chorioptes bovis)、犬猫耳螨(Otodectes cynotis)、疥螨(Sarcoptes scabiei)和猫背肛螨(Notoedres cati)之类的疥螨类、以及犬螺形螨(Demodex canis)之类的螺形螨类等。
作为其他防除对象的蚤,可以列举例如属于蚤目(Siphonaptera)的外部寄生性无翅昆虫,更具体而言,可以列举属于人蚤科(Pulicidae)和角叶蚤科(Ceratephyllus)等的蚤类。作为属于人蚤科的蚤类,可以列举例如犬柿头蚤(Ctenocephalides canis)、猫丰节头蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、禽冠蚤(Echidnophagagallinacea)、印鼠客蚤(Xenopsylla cheopis)、缓慢细蚤(Leptopsylla segnis)、欧洲鼠蚤(Nosopsyllus fasciatus)和不等单蚤(Monopsyllus anisus)等。
作为另外其他防除对象的动物的外寄生物,可以列举例如牛血虱(Haematopinuseurysternus)、马驴血虱(Haematopinus asini)、羊虱(Dalmalinia ovis)、牛颚虱(Linognathus vituli)、猪血虱(Haematopinus suis)、阴虱(Phthirus pubis)和头虱(Pediculus capitis)之类的吸虱类、以及犬啮毛虱(Trichodectes canis)之类的羽虱类、三角虻(Tabanus trigonus)、尖喙库蠓(Culicoides schultzei)和饰蚋(Simuliumornatum)之类的吸血性双翅目害虫等。另外,作为动物的内寄生物,可以列举例如肺虫、鞭虫、结节虫、胃内寄生虫、蛔虫和丝虫类之类的线虫类、孟松裂头绦虫、阔节裂头绦虫、瓜实绦虫、多头绦虫、细粒棘球绦虫和多房棘球绦虫之类的绦虫类、日本血吸虫和肝片形吸虫之类的吸虫类、以及球虫、疟原虫、肠肉孢子虫、弓形虫和隐孢子虫之类的原生动物等。
需要说明的是,由上述可知,本发明化合物不仅能够驱除农业园艺用害虫,而且能够广泛地驱除卫生害虫。
以本发明的通式(I)所示的稠杂环化合物或其盐类作为有效成分的农业园艺用杀虫剂对于危害水田作物、旱田作物、果树、蔬菜、其他作物和花卉等的上述害虫具有显著的防除效果,因此,通过与预测发生害虫的时期相应地在害虫的发生前或确认发生了害虫的时刻对育苗设施、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,能够发挥本发明的农业园艺用杀虫剂的所期望的效果。其中,优选的使用方式是利用所谓的渗透转移性的施用,即,对作物、花卉等的育苗土壤、移植时的植穴土壤、根部、灌溉水、水耕栽培中的栽培水等进行处理,从根经由土壤或者不经由土壤吸收本发明化合物。
可以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,可以列举例如谷类(例如,稻、大麦、小麦、黑麦、燕麦、玉米等)、豆类(大豆、小豆、蚕豆、豌豆、菜豆、花生等)、果树/果实类(苹果、柑橘类、梨、葡萄、桃、李子、樱桃、胡桃、栗子、杏仁、香蕉等)、叶/果菜类(甘蓝、番茄、菠菜、绿花椰菜、生菜、洋葱、葱(细香葱、北葱)、青椒、茄子、草莓、胡椒、秋葵、韭菜等)、根菜类(胡萝卜、马铃薯、番薯、芋头、萝卜、芜菁、藕、牛蒡、蒜、薤等)、加工用作物(棉、麻、甜菜、蛇麻、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(野茅、高粱、梯牧草、三叶草、紫花苜蓿等)、草坪植物类(高丽芝草、糠穗草等)、香料等观赏用作物(薰衣草、迷迭香、百里香、欧芹、胡椒、姜等)、花卉类(菊花、蔷薇、康乃馨、兰花、郁金香、百合等)、庭木(银杏、樱花类、青木等)、林木(冷杉类、银枞类、松类、柏、杉、桧、桉等)等植物。
上述“植物”中也包含利用经典的育种法赋予了对异唑草酮等HPPD抑制剂、咪草烟、噻磺隆甲酯等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、烯禾啶等乙酰CoA羧化酶抑制剂、溴苯腈、麦草畏、2,4-D等除草剂的抗性的植物、或利用基因重组技术赋予了抗性的植物。
作为利用经典的育种法赋予了抗性的“植物”的例子,有对咪草烟等咪唑啉酮类ALS抑制型除草剂具有抗性的油菜、小麦、向日葵、稻,已经以Clearfield(注册商标)的商品名在售卖。还有同样利用经典的育种法得到的对噻吩磺隆甲酯等磺酰脲类ALS抑制型除草剂具有抗性的大豆,已经以STS大豆的商品名在售卖。作为同样利用经典的育种法得到的赋予了对三酮肟类、芳氧基苯氧基丙酸类除草剂等乙酰CoA羧化酶抑制剂的抗性的植物的例子,有SR玉米等。
另外,赋予了对乙酰CoA羧化酶抑制剂的抗性的植物记载在Proc.Natl.Acad.Sci.USA)87卷、7175~7179页(1990年)等中。另外,赋予了对乙酰CoA羧化酶抑制剂的抗性的突变乙酰CoA羧化酶报道于Weed Science 53卷、728~746页(2005年)等中,通过利用基因重组技术将这种突变乙酰CoA羧化酶基因导入到植物中或者在植物乙酰CoA羧化酶中导入与抗性赋予相关的突变,能够制作出对乙酰CoA羧化酶抑制剂具有抗性的植物,此外,利用以嵌合修复技术(Gura T.1999.Repairing the Genome’s SpellingMistakes.Science 285:316-318.)为代表的、将导入有碱基置换突变的核酸导入植物细胞内从而在植物的乙酰CoA羧化酶基因、ALS基因等导入定点氨基酸置换变异的技术,能够制作出对乙酰CoA羧化酶抑制剂、ALS抑制剂等具有抗性的植物,对于这些植物也可以使用本发明的农业园艺用杀虫剂。
此外,作为在基因重组植物中表达的毒素,可以列举蜡样芽胞杆菌、日本甲虫芽胞杆菌来源的杀虫性蛋白;苏云金芽孢杆菌来源的Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C等δ-内毒素、VIP1、VIP2、VIP3或VIP3A等杀虫蛋白;线虫来源的杀虫蛋白;蝎毒素、蜘蛛毒素、蜂毒素或昆虫特异的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、马铃薯贮藏蛋白、胱抑素、木瓜蛋白酶抑制剂等蛋白酶抑制剂;甜菜碱、玉米-RIP、相思豆毒蛋白、丝瓜核糖体失活蛋白、皂素、异株泻根毒蛋白等核糖体失活蛋白(RIP);3-羟基类固醇氧化酶、蜕皮素-UDP-葡糖基转移酶、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;联苄合酶;壳多糖酶;葡聚糖酶等。
另外,作为在这种基因重组植物中表达的毒素,还包含Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9C、Cry34Ab或Cry35Ab等δ-内毒素蛋白、VIP1、VIP2、VIP3或VIP3A等杀虫蛋白的混合毒素、部分缺失的毒素、经修饰的毒素。混合毒素是使用重组技术利用这些蛋白的不同结构域的新的组合而制作出来的。作为部分缺失的毒素,已知有使氨基酸序列的一部分缺失的Cry1Ab。作为经修饰的毒素,有天然型毒素的1个或多个氨基酸被置换而得到的毒素。
这些毒素的例子和能够合成这些毒素的重组植物记载在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。
这些重组植物中含有的毒素特别地赋予植物以对甲虫目害虫、半翅目害虫、双翅目害虫、鳞翅目害虫、线虫类的抗性。本发明的农业园艺用杀虫剂可以与这些技术组合使用,或者也可以系统化使用。
为了防除各种害虫,将有效防除害虫或线虫的量的本发明的农业园艺用杀虫剂直接或者以用水等适当稀释或使其悬浮的形式使用于预测发生该害虫和线虫的植物即可,例如,对于在果树、谷类、蔬菜等中发生的害虫和线虫,除了可以散布于茎叶部以外,还可以将种子浸渍在药剂中、对种子进行粉衣、进行过氧化钙(カルパー)处理等种子处理、土壤全层混合、垄沟施用、床土混合、穴盘苗处理、植穴处理、根部处理、施顶肥、稻箱处理、水面施用等对土壤等进行处理而从根进行吸收来使用。此外,还可以通过在培养液(水耕)栽培中向培养液中施用、烟熏或注入树干等来使用。
此外,将有效防除害虫的量的本发明的农业园艺用杀虫剂直接或者以用水等适当稀释、或使其悬浮的形式使用于预测发生该害虫的场所即可,例如,除了可以散布于储粮害虫、住宅害虫、卫生害虫、森林害虫等以外,还可以用于对住宅建材进行涂布、作为烟熏剂、饵剂等使用。
作为种子处理的方法,可以列举例如将液状或固体状的制剂在进行稀释或不进行稀释的情况下以液体状态浸渍种子而使药剂渗透的方法;将固体制剂或液体制剂与种子混合,对种子进行粉衣处理而使其附着于种子表面的方法;将固体制剂或液体制剂与树脂、聚合物等附着性载体混合并包覆种子的方法;在播种的同时将固体制剂或液体制剂散布于种子附近的方法;等。
进行该种子处理的“种子”是指植物的繁殖中使用的栽培初期的植物体,例如,除了种子以外,还可以列举球茎、块茎、种块、株芽、气生块茎、鳞茎或者扦插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,特别是使根生长的支持体,其材质没有特别限制,只要是能够使植物生长的材质即可,可以为所谓的土壤、育苗垫、水等,作为具体的材料,例如可以为砂、浮石、蛭石、硅藻土、琼脂、凝胶状物质、高分子物质、石棉、玻璃棉、木屑、树皮等。
作为对作物茎叶部或者储粮害虫、住宅害虫、卫生害虫或森林害虫等的散布方法,可以列举将乳剂、悬浮剂等液体制剂或者可湿性剂或可湿性颗粒剂等固体制剂用水适当稀释而进行散布的方法、对粉剂进行散布的方法、或烟熏等。
作为对土壤的施用方法,可以列举例如将液体制剂在用水稀释或未稀释的情况下施用于植物体的根部或育苗用苗床等的方法;将颗粒剂散布到植物体的根部或用于育苗的苗床等的方法;在播种前或移植前散布粉剂、可湿性剂、可湿性颗粒剂、颗粒剂等并与土壤整体混合的方法;在播种前或种植植物体之前将粉剂、可湿性剂、可湿性颗粒剂、颗粒剂等散布到植穴、垄沟等中的方法等。
作为对水稻育苗箱的施用方法,剂型有时根据例如播种时施用、绿化期施用、移植时施用等施用时期而不同,以粉剂、可湿性颗粒剂、颗粒剂等剂型进行施用即可。也可以通过与培土混合来施用,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,床土混合、覆土混合、与培土整体的混合等。也可以简单地将培土与各种制剂交替地形成层状来施用。
作为对水田的施用方法,通常将大粒剂、袋剂(パック剤)、颗粒剂、可湿性颗粒剂等固体制剂、悬浮剂、乳剂等液体制剂散布于浸水状态的水田中。此外,在插秧时,也可以将适当的制剂直接地或混合到肥料等中来散布、注入到土壤中。另外,也可以在进水口、灌溉装置等水田中的水的流入源处利用乳剂、悬浮剂等药液伴随水的供给省力地施用。
对于旱田作物,可以在从播种到育苗期的期间对接近种子或植物体的栽培载体等进行处理。对于直接播种于旱田的植物而言,除了对种子进行直接处理以外,优选对栽培中的植物的根部进行处理。可以使用颗粒剂进行散布处理或者将用水稀释或未稀释的药剂以液态进行灌注处理等。将颗粒剂与播种前的栽培载体混合后再进行播种也是优选的处理。
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,优选对育苗用苗床进行制成液态的药剂的灌注处理或颗粒剂的散布处理。另外,在定植时用颗粒剂对植穴进行处理或者混合到移植场所附近的栽培载体中也是优选的处理。
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适合于使用的形状来使用。
即,对于本发明的通式(I)所示的稠杂环化合物或其盐类,使其溶解、分离、悬浮、混合、浸渗、吸附或附着于适当的惰性载体,或者根据需要使其与助剂一起以适当的比例配合后溶解、分离、悬浮、混合、浸渗、吸附或附着于适当的惰性载体,从而制剂为适当的剂型、例如悬浮剂、乳剂、液剂、可湿性剂、可湿性颗粒剂、颗粒剂、粉剂、片剂、袋剂等来使用即可。
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)除了有效成分以外,还可以根据需要含有农药制剂或动物寄生生物防除剂中通常使用的添加成分。作为该添加成分,可以列举固体载体、液体载体等载体、表面活性剂、分散剂、润湿剂、粘合剂、赋粘剂、增稠剂、着色剂、扩展剂、展着剂、防冻剂、防结块剂、崩解剂、防分解剂等。此外,可以根据需要使用防腐剂、植物片等作为添加成分。这些添加成分可以单独使用,另外,也可以将两种以上组合使用。
作为固体载体,可以列举例如石英、粘土、高岭石、叶蜡石、绢云母、滑石、膨润土、酸性白土、凹凸棒土、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,锯屑、椰壳、玉米穗轴、烟草茎等)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,白炭黑)等。它们可以单独使用,另外,也可以将两种以上组合使用。
作为液体载体,可以列举例如甲醇、乙醇、丙醇、异丙醇、丁醇等一元醇类、乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、甘油等多元醇类之类的醇类、丙二醇醚等多元醇化合物类、丙酮、甲乙酮、甲基异丁基酮、二异丁基酮、环己酮等酮类、乙醚、二烷、乙二醇单乙醚、二丙基醚、四氢呋喃等醚类、正链烷烃、环烷烃、异构烷烃、煤油、矿物油等脂肪族烃类、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、四氯化碳等卤代烃类、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、二甲基亚砜等硫化合物类、大豆油、菜籽油、棉籽油、蓖麻油等植物油、水等。它们可以单独使用,另外,也可以将两种以上组合使用。
作为用作分散剂、湿展剂的表面活性剂,可以列举例如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甲醛缩合物、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、聚氧亚烷基苯乙烯基苯基醚、乙炔二醇、聚氧亚烷基加成乙炔二醇、聚氧乙烯醚型有机硅、酯型有机硅、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型表面活性剂、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、萘磺酸的甲醛缩合物的盐、烷基萘磺酸的甲醛缩合物的盐、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型表面活性剂、月桂胺盐酸盐、硬脂胺盐酸盐、油胺盐酸盐、硬脂胺乙酸盐、硬脂基氨基丙胺乙酸盐、烷基三甲基氯化铵、烷基二甲基苯扎氯铵等烷基胺盐等阳离子表面活性剂、氨基酸型或甜菜碱型等的两性表面活性剂等。这些表面活性剂可以单独使用,另外,也可以将两种以上组合使用。
作为粘合剂、赋粘剂,可以列举例如羧甲基纤维素或其盐、糊精、水溶性淀粉、黄原胶、瓜尔胶、蔗糖、聚乙烯基吡咯烷酮、阿拉伯胶、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸钠、平均分子量6000~20000的聚乙二醇、平均分子量10万~500万的聚环氧乙烷、磷脂(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、交联聚乙烯基吡咯烷酮、马来酸与苯乙烯类的共聚物、(甲基)丙烯酸类共聚物、由多元醇构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、萜烯、聚酰胺树脂、聚丙烯酸盐、聚氧乙烯、蜡、聚乙烯基烷基醚、烷基苯酚甲醛缩合物、合成树脂乳液等。
作为增稠剂,可以列举例如黄原胶、瓜尔胶、迪特胶、羧甲基纤维素、聚乙烯基吡咯烷酮、羧基乙烯基聚合物、丙烯酸类聚合物、淀粉化合物、多糖类之类的水溶性聚合物、高纯度膨润土、气相二氧化硅(fumed silica,白炭黑)之类的无机微粉等。
作为着色剂,可以列举例如氧化铁、氧化钛、普鲁士蓝之类的无机颜料、茜素染料、偶氮染料、金属酞菁染料之类的有机染料等。
作为防冻剂,可以列举例如乙二醇、二乙二醇、丙二醇、甘油等多元醇类等。
作为用于防止结块、促进崩解的助剂,可以列举例如淀粉、天冬氨酸、甘露糖、半乳糖等多糖类、聚乙烯基吡咯烷酮、气相二氧化硅(fumed silica,白炭黑)、酯胶、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、聚乙烯基吡咯烷酮、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,可以列举例如沸石、生石灰、氧化镁之类的干燥剂、酚化合物、胺化合物、硫化合物、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,可以列举例如山梨酸钾、1,2-苯并噻唑啉-3-酮等。
还可以进一步根据需要使用功能性展着剂、胡椒基丁醚等代谢分解抑制剂等活性增强剂、丙二醇等防冻剂、BHT等抗氧化剂、紫外线吸收剂等其他助剂。
有效成分化合物的配合比例可以根据需要来增减,在本发明的农业园艺用杀虫剂100重量份中,从0.01~90重量份的范围适当选择使用即可,例如,在制成粉剂、颗粒剂、乳剂或可湿性剂的情况下,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%)是适当的。
本发明的农业园艺用杀虫剂的使用量根据例如目的、对象害虫、作物的生长状況、害虫的发生倾向、气候、环境条件、剂型、施用方法、施用场所、施用时期等各种因素而变动,作为有效成分化合物,根据目的从每10公亩为0.001g~10kg、优选为0.01g~1kg的范围内适当选择即可。
本发明的农业园艺用杀虫剂也可以出于扩大防除对象病害虫、防除适合期或者减少药量的目的而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,另外,也可以根据使用情况与除草剂、植物生长调节剂、肥料等混合使用。
作为出于该目的而使用的其他农业园艺杀虫剂、杀螨剂、杀线虫剂,可以例示例如:3,5-二甲苯基甲基氨基甲酸酯(3,5-xylyl methylcarbamate(XMC))、苏云金芽孢杆菌(Bacillus thuringienses:例如,苏云金杆菌占泽亚种(Bacillus thuringiensesaizawai)、苏云金杆菌以色列亚种(Bacillus thuringienses israelensis)、苏云金杆菌日本亚种(Bacillus thuringienses japonensis)、苏云金杆菌库斯塔克亚种(Bacillusthuringienses kurstaki)、苏云金杆菌拟步行甲亚种(Bacillus thuringiensestenebrionis)等)所生成的晶体蛋白毒素、BPMC、Bt毒素类杀虫性化合物、杀螨酯(chlorfenson:CPCBS)、二氯二异丙基醚(dichlorodiisopropyl ether:DCIP)、1,3-二氯丙烯(1,3-Dichloropropene:D-D)、DDT、NAC、O-4-二甲基氨磺酰基苯基O,O-二乙基硫代磷酸酯(O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate:DSP)、O-乙基-O-4-硝基苯基苯基硫代磷酸酯(O-ethyl O-4-nitrophenyl phenylphosphonothioate:EPN)、异氰脲酸三丙酯(tripropylisocyanurate: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)、阿维菌素(abamectin)、阿维菌素B(avermectin-B)、横胺螨酯(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)、丙硫多菌灵(albendazole)、烯丙菊酯(allethrin)、氯唑磷(isazofos)、艾沙米多福(isamidofos)、异美沙同磷(isoamidofos)、唑磷(isoxathion)、异柳磷(isofenphos)、异丙威(isoprocarb:MIPC)、伊维菌素(ivermectin)、新烟磷(imicyafos)、吡虫啉(imidacloprid)、炔咪菊酯(imiprothrin)、茚虫威(indoxacarb)、S-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)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、甲埃玛霉素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、硫丹(endosulfan)、右旋烯炔菊酯(empenthrin)、杀线威(oxamyl)、亚砜磷(oxydemeton-methyl)、异亚砜磷(oxydeprofos:ESP)、奥苯达唑(oxibendazole)、奥芬达唑(oxfendazole)、油酸钾(Potassium oleate)、油酸钠(sodium oleate)、
硫线磷(cadusafos)、杀螟丹(cartap)、甲萘威(carbaryl)、丁硫克百威(carbosulfan)、克百威(carbofuran)、精高效氯氟氰菊(gamma-cyhalothrin)、灭杀威(xylylcarb)、喹硫磷(quinalphos)、烯虫炔酯(kinoprene)、灭螨猛(chinomethionat)、硫线磷(cloethocarb)、除线威(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)、溴虫清(chlorphenapyr)、杀螨酯(chlorfenson)、毒虫畏(chlorfenvinphos)、氟啶脲(chlorfluazuron)、乙酯杀螨醇(chlorobenzilate)、氯苯甲酸酯(chlorobenzoate)、开乐散(三氯杀螨醇:dicofol)、蔬果磷(salithion)、杀螟腈(cyanophos:CYAP)、丁醚脲(diafenthiuron)、除线特(diamidafos)、溴氰虫酰胺(cyantraniliprole)、高效反式氯氰菊酯(theta-cypermethrin)、遍地克(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(dinotefuran)、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)、多杀霉素(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)、ζ-氯氰菊酯(zeta-cypermethrin)、二嗪磷(diazinon)、氟胺氰菊酯(tau-fluvalinate)、棉隆(dazomet)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、硫双威(thiodicarb)、杀虫环(thiocyclam)、杀虫单(thiosultap)、杀虫双(thiosultap-sodium)、虫线磷(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)、氟苯脲(teflubenzuron)、甲基内吸磷(demeton-S-methyl)、双硫磷(temephos)、溴氰菊酯(deltamethrin)、特丁硫磷(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)、杀铃脲(triflumuron)、唑虫酰胺(tolfenpyrad)、
二溴磷(naled:BRP)、硝虫噻嗪(nithiazine)、烯啶虫胺(nitenpyram)、氟酰脲(novaluron)、多氟脲(noviflumuron)、烯虫乙酯(hydroprene)、氟吡唑虫(vaniliprole)、蚜灭磷(vamidothion)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、苄螨醚(halfenprox)、氯虫酰肼(halofenozide)、双二氟虫脲(bistrifluron)、杀虫双(bisultap)、氟蚁腙(hydramethylnon)、羟丙基淀粉(hydroxy propyl starch)、乐杀螨(binapacryl)、联苯肼酯(bifenazate)、联苯菊酯(bifenthrin)、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclorfos)、吡嗪氟虫腈(pyrafluprole)、哒嗪硫磷(pyridafenthion)、哒螨灵(pyridaben)、啶虫醚(pyridalyl)、氟虫吡喹(pyrifluquinazon)、吡啶氟虫腈(pyriprole)、吡丙醚(pyriproxyfen)、抗蚜威(pirimicarb)、嘧螨醚(pyrimidifen)、甲基嘧啶磷(pirimiphos-methyl)、除虫菊素(pyrethrins)、氟虫腈(fipronil)、喹螨醚(fenazaquin)、苯线磷(fenamiphos)、溴螨酯(phenisobromolate)、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)、右旋炔丙菊酯(prallethrin)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、啶蜱脲(fluazuron)、氟噻虫砜(fluensulfone)、氟环脲(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(flufenoprox)、苄螨醚(fluproxyfen)、溴氟菊酯(flubrocythrinate)、氟虫酰胺(flubendiamide)、氟氯苯菊酯(flumethrin)、嘧虫胺(flurimfen)、丙硫磷(prothiofos)、普垂菊酯(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)、乙体氟氯氰菊酯(beta-cyfluthrin)、氟铃脲(hexaflumuron)、噻螨酮(hexythiazox)、庚烯磷(heptenophos)、氯菊酯(permethrin)、异噻虫唑(benclothiaz)、虫威(bendiocarb)、杀虫磺(bensultap)、苯螨特(benzoximate)、丙硫克百威(benfuracarb)、
辛硫磷(phoxim)、伏杀硫磷(phosalone)、噻唑磷(fosthiazate)、丁硫环磷(fosthietan)、磷胺(phosphamidon)、磷虫威(phosphocarb)、亚胺硫磷(phosmet:PMP)、浏阳霉素复合物(polynactins)、伐虫脒(formetanate)、安硫磷(formothion)、甲拌磷(phorate)、机油(machine oil)、马拉硫磷(malathion)、米尔倍霉素(milbemycin)、米尔倍霉素A(milbemycin-A)、弥拜菌素(milbemectin)、灭蚜磷(mecarbam)、甲亚砜磷(mesulfenfos)、灭多威(methomyl)、四聚乙醛(metaldehyde)、氰氟虫腙(metaflumizone)、甲胺磷(methamidophos)、安百亩(metam-ammonium)、威百亩(metam-sodium)、甲硫威(methiocarb)、杀扑磷(methidathion:DMTP)、敌线酯(methylisothiocyanate)、甲基新癸酰胺(methylneodecanamide)、甲基对硫磷(methylparathion)、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)、功夫菊酯(lambda-cyhalothrin)、鱼尼汀(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(levamisolhydrochloride)、苯丁锡(fenbutatin oxide)、酒石酸甲噻嘧啶(morantel tartarate)、溴甲烷(methyl bromide)、三环锡(cyhexatin)、氰氨化钙(calcium cyanamide)、石硫合剂(calcium polysulfide)、硫(sulfur)和硫酸烟碱(nicotine-sulfate)等。
作为以同样的目的使用的农业园艺用杀菌剂,可以例示例如:金色制霉素(aureofungin)、阿扎康唑(azaconazole)、氧化福美双(azithiram)、培塔酸(acypetacs)、活化酯(acibenzolar)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敌菌灵(anilazine)、吲唑磺菌胺(amisulbrom)、氨丙磷酸(ampropylfos)、唑嘧菌胺(ametoctradin)、烯丙醇(allyl alcohol)、4-十二烷基-2,6-二甲基吗啉(aldimorph)、代森铵(amobam)、异噻菌胺(isotianil)、氯苯咪菌酮(isovaledione)、吡唑萘菌胺(isopyrazam)、稻瘟灵(isoprothiolane)、种菌唑(ipconazole)、异菌脲(iprodione)、缬霉威(iprovalicarb)、异稻瘟净(iprobenfos)、抑霉唑(imazalil)、双胍辛胺(iminoctadine)、双胍三辛烷基苯磺酸盐(iminoctadine-albesilate)、双胍辛胺乙酸盐(iminoctadine-triacetate)、亚胺唑(imibenconazole)、烯效唑(uniconazole)、烯效唑-P(uniconazole-P)、氯唑灵(echlomezole)、敌瘟磷(edifenphos)、乙环唑(etaconazole)、噻唑菌胺(ethaboxam)、乙嘧酚(ethirimol)、代森硫(etem)、乙氧喹啉(ethoxyquin)、土菌灵(etridiazole)、烯肟菌酯(enestroburin)、氟环唑(epoxiconazole)、霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、8-羟基喹啉铜(copper-8-quinolinolate)、土霉素(oxytetracycline)、8-羟基喹啉铜(copper-oxinate)、咪唑(oxpoconazole)、咪唑富马酸盐(oxpoconazole-fumarate)、喹菌酮(oxolinic acid)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、威百亩(metam-sodium)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)、苯氧喹啉(quinoxyfen)、灭螨猛(quinomethionate)、敌菌丹(captafol)、克菌丹(captan)、精苯霜灵(kiralaxyl)、唑喹菌酮(quinconazole)、五氯硝基苯(quintozene)、双胍辛乙酸盐(guazatine)、硫杂灵(cufraneb)、福美铜氯(cuprobam)、果绿啶(glyodin)、灰黄霉素(griseofulvin)、咪菌酮(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)、四氯喹喔啉(chlorquinox)、氯化苦(chloropicrin)、氯芬唑(chlorfenazole)、氯硝萘(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)、苯氟磺胺(dichlofluanid)、放线菌酮(cycloheximide)、哒菌酮(diclomezine)、氯硝胺(dicloran)、双氯酚(dichlorophen)、二氯萘醌(dichlone)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、烯唑醇(diniconazole)、R-烯唑醇(diniconazole-M)、代森锌(zineb)、二硝巴豆酸酯(dinocap)、二硝酯(dinocton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、消螨通(dinobuton)、消戊酯(dinopenton)、双吡硫翁(dipyrithione)、二苯胺(diphenylamine)、苯醚甲环唑(difenoconazole)、环氟苄酰胺(cyflufenamid)、氟嘧菌胺(diflumetorim)、环菌唑(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、氰菌灵(cypendazole)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、烯酰吗啉(dimethomorph)、霜脲氰(cymoxanil)、醚菌胺(dimoxystrobin)、溴甲烷(methylbromide)、福美辛(ziram)、硅噻菌胺(silthiofam)、链霉素(streptomycin)、螺环菌胺(spiroxamine)、戊苯砜(sultropen)、氟唑环菌胺(sedaxane)、苯酰菌胺(zoxamide)、棉隆(dazomet)代森环(thiadiazin)、噻酰菌胺(tiadinil)、噻二氟(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)、噻菌胺(thifluzamide)、福美双(thiram)、癸磷锡(decafentin)、四氯硝基苯(tecnazene)、叶枯酞(tecloftalam)、福美双联(tecoram)、四氟醚唑(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盐(II)(DBEDC)、十二环吗啉(dodemorph)、肼菌酮(drazoxolon)、三唑醇(triadimenol)、三唑酮(triadimefon)、叶锈特(triazbutil)、咪唑嗪(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)、甲苯氟磺胺(tolylfluanid)、甲基立枯磷(tolclofos-methyl)、纳他霉素(natamycin)、代森钠(nabam)、酞菌酯(nitrothal-isopropyl)、硫氰散(nitrostyrene)、氟苯嘧啶醇(nuarimol)、壬基苯酚磺酸铜(copper nonylphenol sulfonate)、
丙烯酸喹啉酯(halacrinate)、井冈霉素(validamycin)、霜霉灭(valifenalate)超敏蛋白(harpin protein)、联苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、氟吡菌胺(picobenzamide)、硫氯酚(bithionol)、联苯三唑醇(bitertanol)、土菌消(hydroxyisoxazole)、土菌消钾(hydroisoxazole-potassium)、乐杀螨(binapacryl)、联苯(biphenyl)、病花灵(piperalin)、霉灵(hymexazol)、唑菌酯(pyraoxystrobin)、吡喃灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、吡菌磷(pyrazophos)、唑胺菌酯(pyrametostrobin)、氯芬丽(pyriofenone)、啶菌腈(pyridinitril)、啶斑肟(pyrifenox)、吡菌苯威(pyribencarb)、嘧霉胺(pyrimethanil)、氯甲氧吡啶(pyroxychlor)、氯吡呋醚(pyroxyfur)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、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)、四氯苯酞(phthalide)、丁硫啶(buthiobate)、丁胺(butylamine)、乙嘧酚磺酸酯(bupirimate)、麦穗宁(fuberidazole)、灭瘟素(blasticidin-S)、呋吡菌胺(furametpyr)、呋霜灵(furalaxyl)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、氟嘧菌酯(fluoxastrobin)、三氟苯唑(fluotrimazole)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、氟氯菌核利(fluoroimide)、二甲呋酰胺(furcarbanil)、氟唑菌酰胺(fluxapyroxad)、氟喹唑(fluquinconazole)、フル呋菌唑(furconazole)、呋醚(furconazole-cis)、咯菌腈(fludioxonil)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟噻菌净(flutianil)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、糠醛(furfural)、拌种胺(furmecyclox)、氟酰菌胺(flumetover)、氟吗啉(flumorph)、丙氧喹啉(proquinazid)、咪鲜胺(prochloraz)、腐霉利(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、霜霉威(propamocarb)、丙环唑(propiconazole)、丙森锌(propineb)、呋甲硫菌灵(furophanate)、烯丙苯噻唑(probenazole)、糠菌唑(bromuconazole)、六氯丁二烯(hexachlorobutadiene)、己唑醇(hexaconazole)、环己硫磷(hexylthiofos)、吡托沙嗪(bethoxazin)、苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、稻瘟酯(pefurazoate)、醌肟腙(benquinox)、戊菌唑(penconazole)、苯杂吗(benzamorf)、戊菌隆(pencycuron)、苯甲羟肟酸(benzohydroxamic acid)、丙唑草隆(bentaluron)、苯噻硫氰(benthiazole)、苯噻菌胺异丙酯(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、氟唑菌苯胺(penflufen)、
烟酰胺(boscalid)、氯瘟磷(phosdiphen)、三乙膦酸(fosetyl)、三乙膦酸铝(fosetyl-Al)、多氧霉素(polyoxins)、多抗霉素(polyoxorim)、代森福美锌(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)、威百亩钠盐(metam-sodium)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、代森联(metiram)、异硫氰酸甲酯(methyl isothiocyanate)、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)、精甲霜灵(mefenoxam)、二硝巴豆酸酯(meptyldinocap)、灭锈胺(mepronil)、邻酰胺(mebenil)、
碘甲烷(iodomethane)、吡咪唑(rabenzazole)、苯扎氯铵(benzalkoniumchloride)、碱式氯化铜(basic copper chloride)、碱式硫酸铜(basic copper sulfate)、金属银(silver)等无机杀菌剂、次氯酸钠(sodium hypochlorote)、氢氧化铜(cuprichydroxide)、可湿性硫(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(sulfur)、无水硫酸铜(copper sulfate anhydride)、二甲氨基二硫代甲酸镍(nickeldimethyldithiocarbamate)、8-羟基喹啉铜(oxine copper)之类的铜系化合物、硫酸锌(zinc sulfate)、五水硫酸铜(copper sulfate pentahydrate)等。
同样,作为除草剂,可以例示例如: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、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)、S-诱抗酸(abscisic acid)、氨唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、杀草强(amitrole)、环丙吡啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、特草嗪酮(amibuzin)、甲基胺草磷(amiprophos-methyl)、特津酮(ametridione)、莠灭净(ametryn)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、五氯戊酮酸(alorac)、异隆(isouron)、丁咪酰胺(isocarbamid)、异氯草酮(isoxachlortole)、异草醚(isoxapyrifop)、异唑草酮(isoxaflutole)、异酰草胺(isoxaben)、异草定(isocil)、异草完隆(isonoruron)、异丙隆(isoproturon)、异丙乐灵(isopropalin)、氮萆草(isopolinate)、丁嗪草酮(isomethiozin)、抗倒胺(inabenfide)、抑草津(ipazine)、三唑酸草胺(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)、咪草酸(imazamethabenz)、咪草甲酯(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)、吲哚丁酸(indolebutyric acid)、烯效唑-P(uniconazole-P)、甘草津(eglinazine)、戊草丹(esprocarb)、胺苯磺隆(ethametsulfuron)、胺苯磺隆甲酯(ethametsulfuron-methyl)、乙丁烯氟灵(ethalfluralin)、硫草敌(ethiolate)、吲熟酯(ethychlozate ethyl)、磺噻隆(ethidimuron)、硝草酚(etinofen)、乙烯利(ethephon)、乙氧磺隆(ethoxysulfuron)、氯氟草醚(ethoxyfen)、乙胺草醚(etnipromid)、乙氧呋草黄(ethofumesate)、乙氧苯草胺(etobenzanid)、三唑磺(epronaz)、抑草蓬(erbon)、草藻灭(endothal)、草酮(oxadiazon)、丙炔草酮(oxadiargyl)、、嗪草酮(oxaziclomefone)、环氧嘧磺隆(oxasulfuron)、草哒松(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)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、唑草酮(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、特胺灵(karbutilate)、カル双酰草胺(carbetamide)、特唑威(carboxazole)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、喹禾灵乙酯(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)、精草铵膦(glufosinate-P)、醚草敏(credazine)、烯草酮(clethodim)、座果酸(cloxyfonac)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、绿麦隆(chlorotoluron)、二氯吡啶酸(clopyralid)、环丁烯草酮(cloproxydim)、调果酸(cloprop)、氯溴隆(chlorbromuron)、氯丁草(clofop)、异草松(clomazone)、氯硝醚(chlomethoxynil)、甲氧除草醚(chlomethoxyfen)、氯甲酰草胺(clomeprop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯酯磺草胺(cloransulam)、丁酰草胺(chloranocryl)、草灭畏(chloramben)、氯酯磺草胺(cloransulam-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆乙酯(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、敌草索(chlorthal)、氯硫酰草胺(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)、氯甲丹(chlorflurenol)、草败死(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)、氰草津(cyanazine)、氰草净(cyanatryn)、燕麦敌(di-allate)、敌草隆(diuron)、二乙除草双(diethamquat)、麦草畏(dicamba)、环莠隆(cycluron)、环草敌(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)、禾草灵(diclofop)、禾草灵甲酯(diclofop-methyl)、苄胺灵(dichlormate)、氯全隆(dichloralurea)、敌草快(diquat)、咯草隆(cisanilide)、2,4-滴硫钠(disul)、环草隆(siduron)、氟硫草定(dithiopyr)、氨氟灵(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)、双苯酰草胺(diphenamid)、枯莠隆(difenoxuron)、戊味禾草灵(difenopenten)、野燕枯(difenzoquat)、洒布净(cybutryne)、环丙津(cyprazine)、三环赛草胺(cyprazole)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、异丙净(dipropetryn)、环酰草胺(cypromid)、牧草快(cyperquat)、赤霉素(gibberellin)、西玛津(simazine)、草灭散(dimexano)、二甲草胺(dimethachlor)、草哒酮(dimidazon)、异戊津(dimethametryn)、二甲吩草胺(dimethenamid)、西草净(simetryn)、西玛通(simeton)、哌草丹(dimepiperate)、隆(dimefuron)、环庚草醚(cinmethylin)、灭草灵(swep)、吖庚磺酯(sulglycapin)、磺草酮(sulcotrione)、菜草畏(sulfallate)、甲磺草胺(sulfentrazone)、磺酰磺隆(sulfosulfuron)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、仲丁通(secbumeton)、稀禾定(sethoxydim)、另丁津(sebuthylazine)、
特草定(terbacil)、杀草隆(daimuron)、棉隆(dazomet)、茅草枯(dalapon)、噻氟隆(thiazafluron)、噻草定(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆甲酯(thiencarbazone-methyl)、仲草丹(tiocarbazil)、嘧草胺(tioclorim)、禾草丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、甜菜安(desmedipham)、敌草净(desmetryn)、四氟隆(tetrafluron)、噻吩草胺(thenylchlor)、牧草胺(tebutam)、丁噻隆(tebuthiuron)、特丁通(terbumeton)、吡喃草酮(tepraloxydim)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、异丁草胺(delachlor)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁津(terbuthylazine)、特丁净(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)、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、茚草酮(tripropindan)、苯磺隆甲酯(tribenuron-methyl)、苯磺隆(tribenuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三甲隆(trimeturon)、萘草胺(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)、氟氯草胺(nipyraclofen)、草不隆(neburon)、哒草伏(norflurazon)、草完隆(noruron)、
燕麦灵(barban)、多效唑(paclobutrazol)、百草枯(paraquat)、对氟隆(parafluron)、氟啶草(haloxydine)、氟吡禾灵(haloxyfop)、高效氟吡甲禾灵(haloxyfop-P)、氟吡甲禾灵(haloxyfop-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯(halosulfuron-methyl)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、氟吡草酮(bicyclopyrone)、双草醚(bispyribac)、双草醚钠盐(bispyribac-sodium)、比达农(pydanon)、唑啉草酯(pinoxaden)、甲酸除草醚(bifenox)、哌草磷(piperophos)、霉灵(hymexazol)、双唑草腈(pyraclonil)、磺酰草吡唑(pyrasulfotole)、苄草唑(pyrazoxyfen)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯(pyrazosulfuron-ethyl)、吡唑特(pyrazolate)、双丙氨酰膦(bilanafos)、吡草醚(pyraflufen-ethyl)、三氯吡啶酚(pyriclor)、哒草醇(pyridafol)、嘧草硫醚(pyrithiobac)、嘧草硫醚钠盐(pyrithiobac-sodium)、哒草特(pyridate)、环酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧磺苯胺(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)、异苯砜(fenoxasulfone)、唑禾草灵(fenoxaprop)、精唑禾草灵(fenoxaprop-P)、唑禾草灵乙酯(fenoxaprop-ethyl)、酚硫杀(phenothiol)、2,4,5-涕丙酸(fenoprop)、酰草隆(phenobenzuron)、噻唑禾草灵(fenthiaprop)、氯苯氧乙醇(fenteracol)、四唑酰草胺(fentrazamide)、甜菜宁(phenmedipham)、甜菜宁乙酯(phenmedipham-ethyl)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁噻隆(buthiuron)、特咪唑草(buthidazole)、丁草敌(butylate)、炔草隆(buturon)、丁烯草胺(butenachlor)、丁苯草酮(butroxydim)、仲丁灵(butralin)、啶嘧磺隆(flazasulfuron)、麦草氟(flamprop)、呋氧草醚(furyloxyfen)、丙炔草胺(prynachlor)、氟嘧磺隆甲酯(primisulfuron-methyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、异丙吡草酯(fluazolate)、氟草烟(fluroxypyr)、氟硫隆(fluothiuron)、氟草隆(fluometuron)、乙羧氟草醚(fluoroglycofen)、氟咯草酮(flurochloridone)、三氟硝草醚(fluorodifen)、氟除草醚(fluoronitrofen)、唑啶草(fluoromidine)、氟唑磺隆(flucarbazone)、氟唑磺隆钠盐(flucarbazone-sodium)、氯乙氟灵(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)、氟苯啶草(flufenican)、氟哒嗪草酯(flufenpyr)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanate)、氟胺草唑(flupoxam)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac)、氟烯草酸戊酯(flumiclorac-pentyl)、炔草胺(flumipropyn)、三氟嗪(flumezin)、氟草隆(fluometuron)、唑嘧磺草胺(flumetsulam)、氟啶草酮(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)、甲硫磺乐灵(prosulfalin)、氟磺隆(prosulfuron)、苄草丹(prosulfocarb)、喔草酸(propaquizafop)、毒草胺(propachlor)、扑灭津(propazine)、敌稗(propanil)、炔苯酰甲胺(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)、丙苯磺隆钠盐(propoxycarbazone-sodium)、环苯草酮(profoxydim)、除草定(bromacil)、溴草敏(brompyrazon)、扑草净(prometryn)、扑灭通(prometon)、溴苯腈(bromoxynil)、溴酚肟(bromofenoxim)、溴丁酰草胺(bromobutide)、糠草腈(bromobonil)、双氟磺草胺(florasulam)、
六氯丙酮(hexachloroacetone)、环嗪酮(hexazinone)、烯草胺(pethoxamid)、草除灵(benazolin)、五氟磺草胺(penoxsulam)、克草敌(pebulate)、氟丁酰草胺(beflubutamid)、灭草敌(vernolate)、黄草伏(perfluidone)、苯唑磺隆(bencarbazone)、胺酸杀(benzadox)、苄草胺(benzipram)、苄基氨基嘌呤(benzylaminopurine)、苯噻隆(benzthiazuron)、双苯嘧草酮(benzfendizone)、地散磷(bensulide)、苄嘧磺隆甲酯(bensulfuron-methyl)、新燕灵(benzoylprop)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟草黄(benzofluor)、灭草松(bentazone)、甲氯酰草胺(pentanochlor)、禾草丹(benthiocarb)、二甲戊灵(pendimethalin)、环戊草酮(pentoxazone)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、蔓草磷(fosamine)、氟磺胺草醚(fomesafen)、甲酰氨基嘧磺隆(foramsulfuron)、氯吡脲(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)、甲基二磺隆(mesosulfuron)、甲基二磺隆甲酯(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、灭莠津(mesoprazine)、格草净(methoprotryne)、吡草胺(metazachlor)、灭草唑(methazole)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、苯嗪草酮(metamitron)、唑酰草胺(metamifop)、威百亩(metam)、氟烯硝草(methalpropalin)、灭草恒(methiuron)、异噻草醚(methiozolin)、甲硫苯威(methiobencarb)、甲基杀草隆(methyldymron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron)、甲磺隆甲酯(metsulfuron-methyl)、氟哒草(metflurazon)、溴谷隆(metobromuron)、吡喃隆(metobenzuron)、醚草通(methometon)、异丙甲草胺(metolachlor)、嗪草酮(metribuzin)、甲哌(mepiquat-chloride)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、庚酰草胺(monalide)、特唑隆(monisouron)、灭草隆(monuron)、一氯乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、禾草敌(molinate)、伐草快(morfamquat)、碘磺隆(iodosulfuron)、碘磺隆甲酯钠盐(iodosulfuron-methyl-sodium)、碘草腈(iodobonil)、碘甲烷(iodomethane)、乳氟禾草灵(lactofen)、利谷隆(linuron)、砜嘧磺隆(rimsulfuron)、环草定(lenacil)、硫氰苯胺(rhodethanil)、过氧化钙(calcium peroxide)、溴甲烷(methyl bromide)等。
另外,作为生物农药,通过与例如核型多角体病毒(Nuclear polyhedrosisvirus,NPV)、颗粒体病毒(Granulosis virus,GV)、细胞质型多角体病毒(Cytoplasmicpolyhedrosis virus,CPV)、昆虫痘病毒(Entomopoxi virus,EPV)等病毒制剂、作为瘤捕单顶孢(Monacrosporium phymatophagum)、小卷蛾斯氏线虫(Steinernema carpocapsae)、昆虫病原型斯氏线虫(Steinernema kushidai)、穿刺巴斯德氏芽菌(Pasteuria penetrans)等的杀虫剂或杀线虫剂利用的微生物农药、作为木素木霉(Trichoderma lignorum)、放射性农杆菌(Agrobacterium radiobactor)、非病原性胡萝卜软腐欧文氏菌(Erwiniacarotovora)、枯草芽孢杆菌(Bacillus subtilis)等的杀菌剂使用的微生物农药、作为野油菜黄单胞菌(Xanthomonas campestris)等的除草剂利用的生物农药等混合使用,能够期待同样的效果。
此外,作为生物农药,还可以与例如丽蚜小蜂(Encarsia formosa)、科列马阿布拉小蜂(Aphidius colemani)、食蚜瘿蚊(Aphidoletes aphidimyza)、豌豆潜叶蝇姬小蜂(Diglyphus isaea)、西伯利亚离颚茧蜂(Dacnusa sibirica)、智利小植绥螨(Phytoseiulus persimilis)、黄瓜钝绥螨(Amblyseius cucumeris)、东亚小花蝽(Oriussauteri)等天敌生物、卵孢白僵菌(Beauveria brongniartii)等微生物农药、(Z)-10-十四碳烯乙酸酯、(E,Z)-4,10-十四碳二烯乙酸酯、(Z)-8-十二碳烯乙酸酯、(Z)-11-十四碳烯乙酸酯、(Z)-13-二十碳-10-酮、14-甲基-1-十八碳烯等信息素组合使用。
以下利用本发明的代表性化合物和制造中间体的制造例更详细地进行说明,但本发明并不限定于这些例子。
[实施例]
参考例1.N-甲基-3-氨基-6-三氟甲基哒嗪的制造
将按照WO/2005/047279记载的方法合成的6-三氟甲基-3-羟基哒嗪(11.5g)、亚硫酰氯(12.5g)、二甲基甲酰胺(1ml)的混合物加热回流3小时。在反应混合物中加入冰水,用乙酸乙酯萃取。将有机层用无水硫酸镁干燥,减压浓缩。将残渣溶解于四氢呋喃(5ml),在冰冷却下滴加到甲胺(40%甲醇溶液、16.2g)中。在室温下搅拌一晚后,在反应混合物中注入水,用乙酸乙酯萃取。将有机层用无水硫酸镁干燥,减压浓缩。将所得到的残渣供于柱层析,得到目标化合物(3’-1)(5.1g)。
物性:150-152℃
参考例2.N-甲基-3-氨基-4-溴-6-三氟甲基哒嗪的合成
将参考例1中制造的N-甲基-3-氨基-6-三氟甲基哒嗪(1.8g)(3’-1)、3,5-二溴乙内酰脲(3.15g)、乙腈(10ml)的混合物加热回流3小时。在反应混合物中注入饱和硫代硫酸氢钠溶液,用乙酸乙酯萃取。将有机层用无水硫酸镁干燥,减压浓缩。将所得到的残渣供于柱层析,得到目标化合物(3’)(0.9g)。
物性:1H-NMR(CDCl3):7.70(s、1H)、5,41(brs、1H)、3,26(d、1H)
制造实施例1-1.
2-(2-氟-4-三氟甲基苯基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-C]哒嗪的制造
将参考例2中制造的N-甲基-3-氨基-4-溴-6-三氟甲基哒嗪(475mg)(3’)、2-氟-4-三氟甲基苯甲酰胺(500mg)(2’)、叔丁醇钾(311mg)、二苯基膦二茂铁二氯化钯(151mg)、甲苯(5ml)的混合物在氩气下加热回流12小时。在反应混合物中注入水,用乙酸乙酯萃取。将有机层用无水硫酸镁干燥,减压浓缩。将所得到的残渣供于柱层析,得到目标化合物(I’-2)(0.16g)。
物性:1H-NMR(CDCl3):8.21(s、1H)、7.97(t、1H)、7.72(d、1H)、7.64(d、1H)、4.12(d、3H)
制造实施例1.
2-(2-乙基硫基-4-三氟甲基苯基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-C]哒嗪(以下简称为1-1)的制造
在制造实施例1-1中制造的2-(2-氟-4-三氟甲基苯基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-C]哒嗪(160mg)(I’-2)和DMF(2ml)的混合物中加入乙硫醇钠(60mg),在100℃下搅拌2小时。自然冷却后,在反应混合物中注入水,用乙酸乙酯萃取。将有机层用无水硫酸镁干燥,减压浓缩。将所得到的残渣供于柱层析,得到目标物(1-1)(183mg)。
物性:1H-NMR(CDCl3):8.20(s、1H)、7.75(s、1H)、7.64(d、2H)、3.99(s、3H)、3.00(dd、2H)、1.26(t、3H)
制造实施例2
2-(2-乙磺酰基-4-三氟甲基苯基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-C]哒嗪(1-3)的制造
将制造实施例1中制造的2-(2-乙基硫基-4-三氟甲基苯基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-C]哒嗪(100mg)(1-1)、乙酸乙酯(3ml)、间氯过苯甲酸(85mg)的混合物在室温下搅拌3小时。在反应混合物中加入10滴甲醛二甲基缩硫醛硫氧化物(ホルムアルデヒドジメチルジチオアセタールーS-オキシド),减压浓缩。将所得到的残渣供于柱层析,得到目标化合物(1-3)(87mg)。
物性:161-163℃
以下示出制剂的实施例,但不限于此。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(I) 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(I) 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,添加适量的水进行混炼,造粒,干燥,制成颗粒剂。
制剂例4.
将以上物质均匀地混合粉碎,制成可湿性剂。
接着示出本发明的试验例,但不限于此。
试验例1.
对桃蚜(Myzus persicae)的防除价试验
在直径8cm、高度8cm的塑料盆中种植白菜,使桃蚜繁殖,考察各盆的寄生虫数。使本发明的通式(I)所示的稠杂环化合物或其盐类分散于水中,稀释为500ppm的药液,将该药液散布到盆栽白菜的茎叶上,风干后,将盆保存于温室中,在药剂散布后第6天考察各白菜上寄生的桃蚜的寄生虫数,利用下式算出防除价,按照下述判定基准进行判定。
防除价=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:无处理区的散布前寄生虫数
C:无处理区的散布后寄生虫数
判定基准
A···防除价100%
B···防除价99%~90%
C···防除价89%~80%
D···防除价79%~50%
其结果,本发明化合物的1-1、1-2、1-3、1-6、1-10、1-12、1-13、1-14、1-15、1-16、1-18、1-33、1-34、1-35、1-36、1-37、1-39、1-42、1-61、1-62、1-63、1-66、2-10、2-11、2-12、3-7、3-52、4-1、4-2、4-3、4-4、4-5、4-6、4-9、4-12、4-15、4-18、5-1、5-7、5-8、5-9、5-10、5-11、5-13、6-1、6-12、6-13、6-14和6-15显示出A的活性。
试验例2.对灰飞虱(Laodelphax striatella)的杀虫试验
使本发明的通式(I)所示的稠杂环化合物或其盐类分散于水中,稀释为500ppm的药液,将稻苗(品种:日本晴)在该药液中浸渍30秒钟,风干后放入玻璃试验管中,各接种10只三龄灰飞虱后,用棉花塞住,在接种8天后考察生死虫数,利用下式算出校正死虫率,按照试验例1的判定基准进行判定。
其结果,本发明化合物的1-1、1-2、1-3、1-6、1-10、1-12、1-13、1-14、1-15、1-16、1-18、1-33、1-34、1-35、1-36、1-37、1-39、1-42、1-61、1-62、1-63、1-64、1-66、2-12、4-1、4-2、4-3、4-4、4-5、4-6、4-9、4-12、4-15、4-18、5-1、5-3、5-7、5-8、5-9、5-10、5-13、6-1、6-12、6-13、6-14和6-15显示出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将以本发明的通式(I)所示的稠杂环化合物作为有效成分的药剂稀释为500ppm而得到的药液中浸渍约30秒钟,风干后在25℃的恒温室内静置。在药液浸渍6天后考察孵化虫数,利用下式算出死虫率,按照试验例1的判定基准进行判定。1区10只重复3次。
其结果,本发明化合物的1-1、1-2、1-3、1-6、1-10、1-12、1-13、1-14、1-15、1-16、1-18、1-33、1-34、1-35、1-36、1-37、1-39、1-42、1-61、1-62、1-63、1-64、1-66、2-1、2-2、2-12、3-1、3-7、4-1、4-2、4-3、4-4、4-5、4-6、4-9、4-12、4-15、4-18、5-1、5-3、5-7、5-8、5-9、5-10、5-13、6-1、6-12、6-13、6-14和6-15显示出A的活性。
产业上的可利用性
本发明的化合物对范围广泛的农业园艺用害虫具有优良的防除效果,是很有用的。
Claims (11)
1.一种通式(I)所示的稠杂环化合物及其盐类,
式中,R1表示
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a6)卤代(C3-C6)环烷基;
(a7)卤代(C2-C6)链烯基;
(a8)卤代(C2-C6)炔基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a12)卤代(C3-C6)环烷基(C1-C6)烷基;
(a13)(C1-C6)烷氧基卤代(C1-C6)烷基;
(a14)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a16)(C1-C6)烷基亚磺酰基(C1-C6)烷基;
(a17)(C1-C6)烷基磺酰基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基,其中,二(C1-C6)烷基氨基的烷基相同或不同;
(a21)苯基(C1-C6)烷基;或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2表示
(b1)卤素原子;
(b2)氰基;
(b3)硝基;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b9)卤代(C3-C6)环烷基;
(b10)卤代(C2-C6)链烯基;
(b11)卤代(C2-C6)炔基;
(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(C1-C6)烷基;
(b19)卤代(C1-C6)烷氧基(C1-C6)烷基;
(b20)(C3-C6)环烷基(C1-C6)烷基;
(b21)卤代(C3-C6)环烷基(C1-C6)烷基;
(b22)(C1-C6)烷氧基卤代(C1-C6)烷基;
(b23)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(b24)氢原子;
(b25)(C1-C6)烷氧基;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b28)(C1-C6)烷基氨基;
(b29)二(C1-C6)烷基氨基,其中,二(C1-C6)烷基的烷基相同或不同;
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基,其中,三(C1-C6)烷基甲硅烷基的烷基相同或不同;
R3表示
(c1)氢原子;
(c2)卤素原子;
(c3)氰基;
(c4)硝基;
(c5)(C1-C6)烷基;
(c6)(C1-C6)烷氧基;
(c7)(C2-C6)链烯基氧基;
(c8)(C2-C6)炔基氧基;
(c9)卤代(C1-C6)烷基;
(c10)卤代(C1-C6)烷氧基;
(c11)卤代(C2-C6)链烯基氧基;
(c12)卤代(C2-C6)炔基氧基;
(c13)(C1-C6)烷氧基(C1-C6)烷基;
(c14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(c15)(C3-C6)环烷基(C1-C6)烷基;
(c16)卤代(C3-C6)环烷基(C1-C6)烷基;
(c17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(c18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
R4表示
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)硝基;
(d5)(C1-C6)烷基;
(d6)(C1-C6)烷氧基;
(d7)(C2-C6)链烯基氧基;
(d8)(C2-C6)炔基氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)卤代(C2-C6)链烯基氧基;
(d12)卤代(C2-C6)炔基氧基;
(d13)(C1-C6)烷氧基(C1-C6)烷基;
(d14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d15)(C3-C6)环烷基(C1-C6)烷基;
(d16)卤代(C3-C6)环烷基(C1-C6)烷基;
(d17)(C1-C6)烷氧基卤代(C1-C6)烷基;
(d18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d23)苯基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;
(d25)(C1-C6)烷基亚磺酰基;
(d26)(C1-C6)烷基磺酰基;
(d27)卤代(C1-C6)烷基亚磺酰基;或
(d28)卤代(C1-C6)烷基磺酰基;
R5表示
(e1)氢原子;
(e2)甲酰基;
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e6)卤代(C3-C6)环烷基;
(e7)(C1-C6)烷基磺酰基;
(e8)卤代(C1-C6)烷基磺酰基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(e11)(C1-C6)烷氧基卤代(C1-C6)烷基;
(e12)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
(e13)氨基;或
(e14)(C1-C6)烷氧基;
A1、A2和A3相同或不同,表示氮原子或C-R6基,其中,R6表示(f1)氢原子;
(f2)卤素原子;
(f3)氰基;
(f4)硝基;
(f5)甲酰基;
(f6)(C1-C6)烷基;
(f7)(C1-C6)烷氧基;
(f8)(C2-C6)链烯基氧基;
(f9)(C2-C6)炔基氧基;
(f10)(C3-C6)环烷氧基;
(f11)卤代(C1-C6)烷基;
(f12)卤代(C1-C6)烷氧基;
(f13)卤代(C2-C6)链烯基氧基;
(f14)卤代(C2-C6)炔基氧基;
(f15)卤代(C3-C6)环烷氧基;
(f16)(C1-C6)烷硫基;
(f17)(C1-C6)烷基亚磺酰基;
(f18)(C1-C6)烷基磺酰基;
(f19)卤代(C1-C6)烷硫基;
(f20)卤代(C1-C6)烷基亚磺酰基;
(f21)卤代(C1-C6)烷基磺酰基;
(f22)(C1-C6)烷氧基(C1-C6)烷基;
(f23)卤代(C1-C6)烷氧基(C1-C6)烷基;
(f24)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(f25)卤代(C1-C6)烷氧基卤代(C1-C6)烷基;
m表示0、1或2。
2.如权利要求1所述的稠杂环化合物及其盐类,其中,
R1为
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a16)(C1-C6)烷基亚磺酰基(C1-C6)烷基;
(a17)(C1-C6)烷基磺酰基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基,其中,二(C1-C6)烷基氨基的烷基相同或不同;
(a21)苯基(C1-C6)烷基;或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为
(b1)卤素原子;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b12)(C1-C6)烷硫基;
(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;
(b24)氢原子;
(b25)(C1-C6)烷氧基;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b29)二(C1-C6)烷基氨基,其中,二(C1-C6)烷基的烷基相同或不同;
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基,其中,三(C1-C6)烷基甲硅烷基的烷基相同或不同;
R3为(c1)氢原子;
R4为
(d2)卤素原子;
(d5)(C1-C6)烷基;
(d9)卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或
(d26)(C1-C6)烷基磺酰基;
R5为
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e13)氨基;或
(e14)(C1-C6)烷氧基;
A1、A2和A3相同或不同,为氮原子或C-R6基,其中,R6为(f1)氢原子。
3.如权利要求1所述的稠杂环化合物及其盐类,其中,
R1为
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a5)卤代(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a15)(C1-C6)烷硫基(C1-C6)烷基;
(a18)氰基(C1-C6)烷基;
(a19)(C1-C6)烷氧基羰基氧基(C1-C6)烷基;
(a20)二(C1-C6)烷基氨基(C1-C6)烷基,其中,二(C1-C6)烷基氨基的烷基相同或不同;或
(a22)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基(C1-C6)烷基;
R2为
(b1)卤素原子;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b12)(C1-C6)烷硫基;
(b15)卤代(C1-C6)烷硫基;
(b24)氢原子;
(b26)卤代(C1-C6)烷氧基;
(b27)氨基;
(b29)二(C1-C6)烷基氨基,其中,二(C1-C6)烷基的烷基相同或不同;
(b30)(C1-C6)烷基羰基氨基;
(b31)(C1-C6)烷基磺酰基氨基;
(b32)(C1-C6)烷基磺酰基((C1-C6)烷基)氨基;
(b33)(C1-C6)烷氧基羰基;或
(b34)三(C1-C6)烷基甲硅烷基(C2-C6)炔基,其中,三(C1-C6)烷基甲硅烷基的烷基相同或不同;
R3为(c1)氢原子;
R4为
(d2)卤素原子;
(d9)卤代(C1-C6)烷基;
(d19)巯基;
(d20)(C1-C6)烷硫基;
(d21)(C1-C6)烷基羰基硫基;
(d22)卤代(C1-C6)烷硫基;
(d24)在环上具有选自由(a)卤素原子、(b)氰基、(c)硝基、(d)(C1-C6)烷基、(e)(C1-C6)烷氧基、(f)卤代(C1-C6)烷基和(g)卤代(C1-C6)烷氧基组成的组中的1~5个取代基的苯基;或
(d26)(C1-C6)烷基磺酰基;
R5为
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;或
(e9)(C1-C6)烷氧基(C1-C6)烷基;
A1、A2和A3相同或不同,为氮原子或C-R6基,其中,R6为(f1)氢原子。
4.权利要求1~3中任一项所述的稠杂环化合物或其盐类作为农业园艺用杀虫剂的使用。
5.一种农业园艺用杀虫剂的使用方法,其特征在于,使用权利要求4所述的农业园艺用杀虫剂的有效成分对植物或土壤进行处理。
6.一种农业园艺用害虫的防除方法,其特征在于,使用有效量的权利要求4所述的农业园艺用杀虫剂对植物或土壤进行处理。
7.一种外寄生物防除剂,其特征在于,含有权利要求1~3中任一项所述的稠杂环化合物或其盐类作为有效成分。
8.有效量的权利要求1~3中任一项所述的稠杂环化合物或其盐类在制造外寄生物防除剂中的应用。
9.一种杀虫剂,其含有权利要求1~3中任一项所述的稠杂环化合物或其盐类作为有效成分。
10.如权利要求9所述的杀虫剂,其中,所述稠杂环化合物为咪唑并[4,5-C]哒嗪稠杂环化合物。
11.一种通式(I)所示的稠杂环化合物及其盐类,
式中,
R1表示
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C2-C6)链烯基;
(a4)(C2-C6)炔基;
(a5)卤代(C1-C6)烷基;
(a6)卤代(C3-C6)环烷基;
(a7)卤代(C2-C6)链烯基;
(a8)卤代(C2-C6)炔基;
(a9)(C1-C6)烷氧基(C1-C6)烷基;
(a10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(a11)(C3-C6)环烷基(C1-C6)烷基;
(a12)卤代(C3-C6)环烷基(C1-C6)烷基;
(a13)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(a14)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R2表示
(b1)卤素原子;
(b2)氰基;
(b3)硝基;
(b4)(C1-C6)烷基;
(b5)(C3-C6)环烷基;
(b6)(C2-C6)链烯基;
(b7)(C2-C6)炔基;
(b8)卤代(C1-C6)烷基;
(b9)卤代(C3-C6)环烷基;
(b10)卤代(C2-C6)链烯基;
(b11)卤代(C2-C6)炔基;
(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(C1-C6)烷基;
(b19)卤代(C1-C6)烷氧基(C1-C6)烷基;
(b20)(C3-C6)环烷基(C1-C6)烷基;
(b21)卤代(C3-C6)环烷基(C1-C6)烷基;
(b22)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(b23)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R3表示
(c1)氢原子;
(c2)卤素原子;
(c3)氰基;
(c4)硝基;
(c5)(C1-C6)烷基;
(c6)(C1-C6)烷氧基;
(c7)(C2-C6)链烯基氧基;
(c8)(C2-C6)炔基氧基;
(c9)卤代(C1-C6)烷基;
(c10)卤代(C1-C6)烷氧基;
(c11)卤代(C2-C6)链烯基氧基;
(c12)卤代(C2-C6)炔基氧基;
(c13)(C1-C6)烷氧基(C1-C6)烷基;
(c14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(c15)(C3-C6)环烷基(C1-C6)烷基;
(c16)卤代(C3-C6)环烷基(C1-C6)烷基;
(c17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(c18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R4表示
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)硝基;
(d5)(C1-C6)烷基;
(d6)(C1-C6)烷氧基;
(d7)(C2-C6)链烯基氧基;
(d8)(C2-C6)炔基氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)卤代(C2-C6)链烯基氧基;
(d12)卤代(C2-C6)炔基氧基;
(d13)(C1-C6)烷氧基(C1-C6)烷基;
(d14)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d15)(C3-C6)环烷基(C1-C6)烷基;
(d16)卤代(C3-C6)环烷基(C1-C6)烷基;
(d17)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(d18)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
R5表示
(e1)氢原子;
(e2)甲酰基;
(e3)(C1-C6)烷基;
(e4)(C3-C6)环烷基;
(e5)卤代(C1-C6)烷基;
(e6)卤代(C3-C6)环烷基;
(e7)(C1-C6)烷基磺酰基;
(e8)卤代(C1-C6)烷基磺酰基;
(e9)(C1-C6)烷氧基(C1-C6)烷基;
(e10)卤代(C1-C6)烷氧基(C1-C6)烷基;
(e11)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(e12)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
A1、A2和A3相同或不同,表示氮原子或C-R6基,其中,R6表示
(f1)氢原子;
(f2)卤素原子;
(f3)氰基;
(f4)硝基;
(f5)甲酰基;
(f6)(C1-C6)烷基;
(f7)(C1-C6)烷氧基;
(f8)(C2-C6)链烯基氧基;
(f9)(C2-C6)炔基氧基;
(f10)(C3-C6)环烷氧基;
(f11)卤代(C1-C6)烷基;
(f12)卤代(C1-C6)烷氧基;
(f13)卤代(C2-C6)链烯基氧基;
(f14)卤代(C2-C6)炔基氧基;
(f15)卤代(C3-C6)环烷氧基;
(f16)(C1-C6)烷硫基;
(f17)(C1-C6)烷基亚磺酰基;
(f18)(C1-C6)烷基磺酰基;
(f19)卤代(C1-C6)烷硫基;
(f20)卤代(C1-C6)烷基亚磺酰基;
(f21)卤代(C1-C6)烷基磺酰基;
(f22)(C1-C6)烷氧基(C1-C6)烷基;
(f23)卤代(C1-C6)烷氧基(C1-C6)烷基;
(f24)(C1-C6)烷氧基卤代(C1-C6)烷基;或
(f25)卤代(C1-C6)烷氧基卤代(C1-C6)烷基,
m表示0、1或2。
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CN101253174A (zh) * | 2005-08-30 | 2008-08-27 | 住友化学株式会社 | 制备咪唑并[1,2-b]哒嗪化合物的方法 |
JP2012131780A (ja) * | 2010-12-01 | 2012-07-12 | Sumitomo Chemical Co Ltd | ピリミジン化合物およびその有害生物防除用途 |
WO2012086848A1 (en) * | 2010-12-24 | 2012-06-28 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound and use for pest control thereof |
WO2013018928A1 (en) * | 2011-08-04 | 2013-02-07 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound and use thereof for pest control |
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EP2975039B1 (en) | 2018-08-15 |
EP2975039A4 (en) | 2016-07-27 |
TW201514179A (zh) | 2015-04-16 |
CN105051045A (zh) | 2015-11-11 |
AU2014230571B2 (en) | 2018-09-06 |
ES2685587T3 (es) | 2018-10-10 |
BR112015020972B1 (pt) | 2019-12-03 |
JPWO2014142292A1 (ja) | 2017-02-16 |
MX2015013073A (es) | 2016-01-22 |
JP6263166B2 (ja) | 2018-01-17 |
RU2015143842A (ru) | 2017-04-26 |
EP2975039A1 (en) | 2016-01-20 |
UY35421A (es) | 2014-10-31 |
WO2014142292A1 (ja) | 2014-09-18 |
KR20150132401A (ko) | 2015-11-25 |
US9936703B2 (en) | 2018-04-10 |
AU2014230571A1 (en) | 2015-10-15 |
BR112015020972A2 (pt) | 2017-07-18 |
DK2975039T3 (en) | 2018-11-12 |
US20160021886A1 (en) | 2016-01-28 |
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