CN101668733A - 环丙烷羧酸化合物及其在害虫防治中的用途 - Google Patents
环丙烷羧酸化合物及其在害虫防治中的用途 Download PDFInfo
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- CN101668733A CN101668733A CN200880013693A CN200880013693A CN101668733A CN 101668733 A CN101668733 A CN 101668733A CN 200880013693 A CN200880013693 A CN 200880013693A CN 200880013693 A CN200880013693 A CN 200880013693A CN 101668733 A CN101668733 A CN 101668733A
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- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
式(1)代表的酯化合物,其中R代表C1-C4烷基或C3-C4烯基,A代表单键或氧原子,该化合物具有优良的害虫防治效力,并且它可用作害虫防治剂的活性成分。
Description
技术领域
本发明涉及酯化合物及其用途。
背景技术
EP 0926129 A1描述了一类四氟苄酯化合物。
发明内容
本发明的目的是提供具有优良害虫防治效力的化合物。
为寻找具有优良害虫防治效力的化合物,本发明发明人进行了深入研究,结果发现下文中式(1)代表的化合物具有优良害虫防治效力,导致本发明。
即本发明提供:
1.式(1)代表的酯化合物:
其中R代表C1-C4烷基或C3-C4烯基,A代表单键或氧原子(下文称为本发明化合物);
2.上述1的酯化合物,其中A为单键;
3.上述1的酯化合物,其中A为氧原子;
4.一种害虫防治剂,该害虫防治剂含式(1)代表的酯化合物作为活性成分;
5.一种防治害虫的方法,该方法包括将有效量的式(1)代表的酯化合物施用到害虫或害虫栖息的场所;和
6.式(1)代表的酯化合物在防治害虫中的用途。
因为本发明化合物具有优良害虫防治效力,所以它可用作害虫防治剂的活性成分。
实施本发明的方式
在本发明化合物中,有由位于环丙烷环上的两个不对称碳原子形成的异构体和由双键形成的异构体,它们各自和具有任意比例的这些异构体的混合物包括在本发明中。
在本发明中,C1-C4烷基的实例包括甲基、乙基、丙基等,C3-C4烯基的实例包括烯丙基。
本发明化合物的实例包括以下化合物:
1)式(1)代表的化合物,其中环丙烷环1-位的绝对构型为R构型;
2)式(1)代表的化合物,其中环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为反式构型;
3)式(1)代表的化合物,其中环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为顺式构型;
4)式(1)代表的化合物,其中存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
5)式(1)代表的化合物,其中环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为反式构型;
6)式(1)代表的化合物,其中环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为顺式构型;
7)式(1)代表的化合物,其中环丙烷环1-位的绝对构型为R构型,环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为反式构型,且存在于环丙烷环3位取代基上的双键的相对构型为Z构型;
8)式(1)代表的化合物,其中环丙烷环1-位的绝对构型为R构型,环丙烷环1-位的取代基和环丙烷环3-位的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
9)式(1)代表的化合物,所述化合物富集以下的化合物:其中环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
10)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
11)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
12)式(1)代表的化合物,其中R为C1-C4烷基;
13)式(1)代表的化合物,其中R为C3-C4烯基;
14)式(1)代表的化合物,其中R为甲基或烯丙基;
15)式(1)代表的化合物,其中A为单键;
16)式(1)代表的化合物,其中A为氧原子;
17)式(1)代表的化合物,其中R为C1-C4烷基,A为单键;
18)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,且环丙烷环1-位的绝对构型为R构型;
19)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
20)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
21)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
22)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
23)一种化合物,其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
24)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
25)式(1)代表的化合物,其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
26)式(1)代表的化合物,所述化合物富集以下的化合物,其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
27)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为C1-C4烷基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
28)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为C1-C4烷基,A为单键,环丙烷环1位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
29)式(1)代表的化合物,其中R为C3-C4烯基,且A为单键;
30)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,且环丙烷环1-位的绝对构型为R构型;
31)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
32)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
33)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
34)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
35)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
36)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
37)式(1)代表的化合物,其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
38)式(1)代表的化合物,所述化合物富集以下的化合物:其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
39)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
40)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为C3-C4烯基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
41)式(1)代表的化合物,其中R为C1-C4烷基,且A为氧原子;
42)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,且环丙烷环1-位的绝对构型为R构型;
43)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
44)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
45)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
46)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
47)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
48)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
49)式(1)代表的化合物,其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
50)式(1)代表的化合物,所述化合物富集以下的化合物:其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
51)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
52)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为C1-C4烷基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
53)式(1)代表的化合物,其中R为甲基,且A为单键;
54)式(1)代表的化合物,其中R为甲基,A为单键,且环丙烷环1-位的绝对构型为R构型;
55)式(1)代表的化合物,其中R为甲基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
56)式(1)代表的化合物,其中R为甲基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
57)式(1)代表的化合物,其中R为甲基,A为单键,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
58)式(1)代表的化合物,其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
59)式(1)代表的化合物,其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
60)式(1)代表的化合物,其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
61)式(1)代表的化合物,其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
62)式(1)代表的化合物,所述化合物富集以下的化合物:其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
63)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
64)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为甲基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
65)式(1)代表的化合物,其中R为烯丙基,且A为单键;
66)式(1)代表的化合物,其中R为烯丙基,A为单键,且环丙烷环1-位的绝对构型为R构型;
67)式(1)代表的化合物,其中R为烯丙基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
68)式(1)代表的化合物,其中R为烯丙基,A为单键,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
69)式(1)代表的化合物,其中R为烯丙基,A为单键,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
70)式(1)代表的化合物,其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
71)式(1)代表的化合物,其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
72)式(1)代表的化合物,其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
73)式(1)代表的化合物,其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
74)式(1)代表的化合物,所述化合物富集以下的化合物:其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
75)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
76)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为烯丙基,A为单键,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
77)式(1)代表的化合物,其中R为甲基,且A为氧原子;
78)式(1)代表的化合物,其中R为甲基,A为氧原子,且环丙烷环1-位的绝对构型为R构型;
79)式(1)代表的化合物,其中R为甲基,A为氧原子,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
80)式(1)代表的化合物,其中R为甲基,A为氧原子,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
81)式(1)代表的化合物,其中R为甲基,A为氧原子,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
82)式(1)代表的化合物,其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
83)式(1)代表的化合物,其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型;
84)式(1)代表的化合物,其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
85)式(1)代表的化合物,其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为顺式构型,且存在于环丙烷环3-位取代基上的双键的相对构型为Z构型;
86)式(1)代表的化合物,所述化合物富集以下的化合物:其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;
87)式(1)代表的化合物,所述化合物含不小于80%的以下化合物:其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型;和
88)式(1)代表的化合物,所述化合物含不小于90%的以下化合物:其中R为甲基,A为氧原子,环丙烷环1-位的绝对构型为R构型,且环丙烷环1-位上的取代基和环丙烷环3-位上的取代基的相对构型为反式构型。
例如,本发明化合物可通过以下方法制备。
该方法包括使式(2)代表的醇化合物:
其中R代表C1-C4烷基或C3-C4烯基,且A代表单键或氧原子,与式(3)代表的羧酸化合物或其活性衍生物(例如酰卤、酸酐等)反应:
通常,在缩合剂或碱的存在下,在溶剂中进行该反应。
缩合剂的实例包括二环己基碳二亚胺和1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐。
碱的实例包括有机碱例如三乙胺、吡啶、N,N-二乙基苯胺、4-二甲基氨基吡啶和二异丙基乙胺。
溶剂的实例包括烃例如苯、甲苯和己烷;醚例如乙醚和四氢呋喃;和卤代烃例如二氯甲烷、1,2-二氯乙烷和氯苯。
反应时间通常为5分钟-72小时。
反应温度通常为-20℃-100℃(条件是当所用溶剂的沸点低于100℃时,为-20℃至溶剂的沸点),优选-5℃至100℃(条件是当所用溶剂的沸点低于100℃时,为-5℃至溶剂的沸点)。
在反应中,可适当选择使用的式(2)代表的醇化合物与式(3)代表的羧酸化合物或其活性衍生物的摩尔比,但反应优选按等摩尔比或接近等摩尔比的比例进行。
通常,缩合剂或碱可按1摩尔至过量的适当比例,优选相对于1摩尔式(2)代表的醇化合物为1摩尔-5摩尔使用。根据式(3)代表的一类具体羧酸化合物或其活性衍生物(例如式(3)代表的羧酸化合物的相应酰氯化合物、酰溴化合物、酸酐等),适当选择缩合剂或碱。
反应完全后,反应混合物进行常规后处理操作,例如将反应混合物过滤,然后将得到的滤液浓缩;或将反应混合物倾入水中,然后用有机溶剂萃取,将萃取液浓缩,得到本发明化合物。可通过常规方法例如色谱法和蒸馏,将得到的本发明化合物纯化。
式(2)代表的醇化合物为市售产品,或EP 0926129 A1和美国专利号4405640中所述化合物,并可作为市售产品购买,或可按这些出版物所述方法制备。
式(3)代表的羧酸化合物为例如Agr.Biol.Chem.,34,1119(1970)中所述化合物,并可按其中所述方法制备。
本发明化合物对其具有效力的害虫的实例包括节肢动物例如昆虫和螨,尤其是例如以下害虫。
鳞翅目:
螟蛾科例如二化螟(Chilo suppressalis)(二化螟)、稻纵卷叶螟(Cnaphalocrocis medinalis)(稻纵卷叶螟)、印度谷螟(Plodiainterpunctella)(印度谷螟)等;夜蛾科例如斜纹夜蛾(Spodopteralitura)(黄地老虎)、粘虫(Pseudaletia separate)(水稻叶夜蛾)、甘蓝夜蛾(Mamestra brassicae)(甘蓝夜蛾)等;粉蝶科例如菜粉蝶(Pieris rapae)(菜粉蝶)等;卷叶蛾科例如茶小卷叶蛾(Adoxophyes orana)等;
蛀蛾科;潜叶蛾科;毒蛾科;金翅夜蛾科;地老虎属(Agrotis ssp.)例如黄地老虎(Agrotis segetum)(地老虎)、小地老虎(Agrotis ipsilon)(小地老虎)等;实夜蛾(Helicoverpa spp.);棉花实夜蛾属(Heliothis spp.);小菜蛾(Plutella xylostella)(菱纹背蛾);直纹稻弄蝶(Parnara guttata)(直纹稻苞虫);夜蛾趋虫(Tinea pellionella)(袋谷蛾);负袋夜蛾(Tineolabisselliell)(幕谷蛾)等;
双翅目:
蚊科例如淡色库蚊(Culex pipiens pallens)(普通蚊子)、三带啄库蚊(Culex tritaeniorhynchus)等;伊蚊属(Aedes spp.)例如埃及伊蚊(Aedesaegypti)、白蚊伊蚊(Aedes albopictus)等;按蚊属(Anopheles spp.)例如中华按蚊(Anopheles sinensis)等;摇蚊科(摇蚊);蝇科例如家蝇(Muscadomestica)(家蝇)、大家蝇(Muscina stabulans)(厩腐蝇)、夏厕蝇(Fanniacanicularis)(小家厕蝇)等;丽蝇科;麻蝇亚科;花蝇科例如灰地种蝇(Hylemya platura)(灰地种蝇)、葱地种蝇(Delia antique)(葱蝇)等;实蝇科(果蝇);果蝇科(小果蝇);毛蠓科(蛾蝇);蚤蝇科;蚋科(黑蝇);虻科;刺蝇科(厩蝇);蠓科;等;
脉翅目:
德国小蠊(Blattella germanica)(德国蟑螂)、黑胸大蠊(Periplanetafuliginosa)(烟色大蠊)、美洲大蠊(Periplaneta americana)(美洲蟑螂)、褐斑大蠊(Periplaneta brunnea)(褐色大蠊)、东方蜚蠊(Blattaorientalis)(东方蟑螂)等;
膜翅目:
蚁科(蚂蚁);胡蜂科(大黄蜂);肿腿蜂科;叶蜂亚科例如日本玫瑰菜叶蜂(Athalia rosae japonensis)(菜叶蜂)等;
微翅目:
犬栉首蚤(Ctenocephalides canis)、猫蚤(Ctenocephalides felis)、人蚤(Pulex irritans)等;
虱目:
头虱(Pediculus humanus)、阴虱(Phthirus pubis)、人体虱(Pediculushumanus humanus)、人头虱(Pediculus humanus corporis)等;
等翅目:
黄胸散白蚁(Reticulitermes speratus)、台湾乳白蚁(Coptotermesformosanus)等;
半翅目:
飞虱科(飞虱)例如灰飞虱属(Laodelphax striatellus)(小灰飞虱)、褐飞虱(Nilaparvata lugens)(褐水稻飞虱)、白背飞虱(Sogatellafurcifera)(白背稻飞虱)等;角顶叶虫蝉科(叶蝉)例如黑尾叶蝉(Nephotettix cincticeps)(黑尾叶蝉)、二点黑尾叶蝉(Nephotettixvirescens)(黑尾叶蝉)等;蚜科(蚜虫);蝽科(椿象);粉虱科(粉虱);蚧科(蚧);网蝽科(网蝽);木虱科(木虱)等;
鞘翅目:
日本黑皮蠹(Attagenus japonicus);小圆皮蠹(Anthrenus verbasci);叶甲属(Diabrotica spp.)(南瓜十二星叶甲)例如玉米根萤叶甲(Diabrotica virgifera)(玉米根叶甲)、十一星根萤叶甲(Diabroticaundecimpunctata howardi)(南方南瓜十二星叶甲)等;蜣螂科例如赤铜丽金龟(Anomala cuprea)(大绿丽金龟)、豆卷叶(Anomala rufocuprea)(方头绿金龟子)等;象虫科例如玉米象(Sitophilus zeamais)(玉米象鼻虫)、稻米象甲(Lissorhoptrus oryzophilus)(稻水象虫)、棉铃象(Anthonomusgradis grandis)(棉籽象鼻虫)、绿豆象(Callosobruchuys chienensis)(赤豆象鼻虫)等;拟步甲科(拟步甲)例如黄粉虫(Tenebrio molitor)(黄粉虫)、赤拟谷盗(Tribolium castaneum)(赤拟谷盗)等;夜甲科(叶甲虫)例如水稻负泥虫(Oulema oryzae)(稻负泥虫)、黄曲条跳甲(Phyllotretastriolata)(黄宽条跳甲)、印度黄守瓜(Aulacophora femoralis)(黄守瓜)等;窃蠹科(药房甲虫(drugstore beetles));马铃薯瓢虫属(Epilachna spp.)例如茄二十八星瓢虫(Epilachna vigintioctopunctata)(二十八星瓢虫)等;粉蠹科(粉蠹甲虫);长蠹科(伪粉蠹甲虫);天牛科(天牛);梭毒急翅虫(Paederus fuscipes)(隐翅虫)等;
缨翅目:
棕榈蓟马(Thrips palmi)、西花蓟马(Frankliniella occidentalis)、花蓟马(Thrips hawaiiensis)(花蓟马)等;
直翅目:
蝼蛄(Gryllotalpa fossor Scudder)、剑角蝗科(蝗虫)等;
螨:
皮刺螨科例如粉尘螨科(Dermatophagoides farinae)、屋尘螨(Dermatophagoides ptrenyssnus)等;粉螨科例如腐食酪螨(Tyrophagusputrescentiae)(腐食酪螨)、椭圆嗜粉螨(Aleuroglyphus ovatus)(褐色腿干酪螨(brown legged grain mite))等;食甜螨亚科例如隐秘食甜螨(Glycyphagidae privates)、家食甜螨(Glycyphagidae domesticus)、Glycyphagus destructor(杂货店螨(groceries mite))等;肉食螨亚科例如马六甲肉食螨(Cheyletus malaccensis)、马六甲肉食螨(Cheyletusmalaccesis)等;跗线螨科;嗜草螨亚科;单缝甲螨科;叶螨总科例如二斑叶螨(Tetranychus urticae)(二斑叶螨)、神泽氏叶螨(Tetranychuskanzawai)(神泽氏叶螨)、柑橘全爪螨(Panonychus citri)(柑橘红叶螨)、苹果全爪螨(Panonychus ulmi)(苹果红蜘蛛)等;硬蜱科例如长角血蜱(Haemaphysalis longicornis)等。
本发明害虫防治剂可为本发明化合物自身,或其通常为含本发明化合物和惰性载体的制剂。
制剂的实例包括油溶液、可乳化浓缩物、可湿性粉剂、可流动制剂(例如水悬浮液、水乳液)、粉剂、颗粒剂、气雾剂;加热挥发性制剂(例如用于电加热的杀虫剂盘状物、杀虫用垫子;具有用于加热吸收性芯的挥发性制剂)、加热薰剂(例如自燃型薰剂、化学反应型薰剂、多孔陶瓷板薰剂等)、非加热挥发性制剂(例如树脂挥发性制剂、浸渍的纸挥发性制剂)、烟熏制剂(例如生雾)、ULV制剂和毒饵。
配制方法的实例包括以下方法。
[1]将本发明化合物与固体载体、液体载体、气体载体、诱饵等混合的方法,如果需要,加入制剂用表面活性剂和其它助剂。
[2]用本发明化合物浸渍成形固体载体的方法,该固体载体不含活性成分。
[3]将本发明化合物与粉状固体载体混合,任选加入制剂用表面活性剂和其它助剂,然后使得到的混合物成形的方法。
根据制剂类型,这些制剂通常以0.001-95%的重量比含本发明化合物。
用于制剂的载体实例包括固体载体{粘土(例如高岭土、硅藻土、合成水合二氧化硅、膨润土、Fubasami粘土和酸性粘土)、滑石粉、陶瓷、其它无机矿物质(例如绢云母、石英、硫磺、活性碳、碳酸钙、水合二氧化硅和蒙脱石)、化学肥料(例如硫酸铵、磷酸铵、硝酸铵、尿素和氯化铵)等};液体载体{水、醇(例如甲醇和乙醇)、酮(例如丙酮和甲乙酮)、芳烃(例如苯、甲苯、二甲苯、乙苯、甲基萘和苯基二甲苯基乙烷)、脂肪烃(例如己烷、环己烷、煤油和汽油)、酯(例如乙酸乙酯和乙酸丁酯)、腈(例如乙腈和异丁腈)、醚(例如二异丙基醚和二噁烷)、酰胺(例如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺)、卤代烃(二氯甲烷、三氯乙烷和四氯化碳)、二甲亚砜、植物油(例如大豆油和棉籽油)等};和气体载体{氟里昂(flon)气体、丁烷气体、LPG(液化石油气)、二甲醚、二氧化碳气体等}。
表面活性剂的实例包括烷基硫酸酯、烷基磺酸盐、烷基芳基磺酸盐、烷基芳基醚、聚氧乙烯化烷基芳基醚、聚乙二醇醚、多元醇酯和糖醇衍生物。
用于制剂的其它助剂的实例包括粘合剂、分散剂和稳定剂,例如酪蛋白、明胶、多糖(例如淀粉、阿拉伯胶、纤维素衍生物和精氨酸)、木质素衍生物、膨润土、合成水溶性聚合物(例如聚乙烯醇和聚乙烯吡咯烷酮)、聚丙烯酸、BHT(2,6-二叔丁基-4-甲基苯酚)和BHA(2-叔丁基-4-甲氧基苯酚和3-叔丁基-4-甲氧基苯酚的混合物)。
用于杀虫剂盘状物的固体载体的实例包括植物粉末例如木粉和除虫菊(Pyrethrum marc)等,和粘合剂例如Tabu粉末(红楠(Machilusthunbergii)粉末)、淀粉、麸质等的混合物。
用于电热杀虫用垫子的成形固体载体的实例包括配制成板状物的棉绒,和配制成板状物的棉绒和纸浆的混合物原纤维。
用于自燃型薰剂的固体载体的实例包括燃烧生热剂,例如硝酸盐、亚硝酸盐、胍盐、氯酸钾、硝基纤维素、乙基纤维素、木粉等;热分解刺激剂例如碱金属盐、碱土金属盐、重铬酸盐、铬酸盐等;供氧剂例如硝酸钾等;助燃剂例如蜜胺、小麦淀粉等;增量剂例如硅藻土;和粘合剂例如合成糊剂等。
用于化学反应型薰剂的固体载体的实例包括生热剂,例如碱金属硫化物、多硫化物、氢硫化物、氧化钙等;催化剂例如含碳物质、碳化铁、活性粘土等;有机发泡剂例如偶氮二甲酰胺、苯磺酰肼、二硝基五亚甲基四胺、聚苯乙烯、聚氨酯等;和填充剂例如天然纤维片、合成纤维片等。
用于非加热挥发性制剂的固体载体的实例包括热塑性树脂和纸(文件纸(filer paper)、日本纸等)。
用于毒饵的基质材料的实例包括诱饵成分例如系列粉末(serialpowder)、植物油、糖、结晶纤维素等;抗氧化剂例如二丁基羟基甲苯、去甲二氢愈创木酸(guar acetic acid)等;防腐剂例如脱氢乙酸等;防止儿童或宠物误食的试剂例如辣椒粉;和引诱害虫的香料例如奶酪香料、洋葱香料、花生油等。
通常通过将有效量的本发明害虫防治剂形式的本发明化合物施用到害虫或害虫栖息的场所,来实施本发明防治害虫的方法。
施用本发明害虫防治剂的方法实例包括以下方法,可根据本发明害虫防治剂的具体形式、具体使用场所等适当选择该方法。
[1]用本发明害虫防治剂,按照原样处理害虫或害虫栖息的场所的方法。
[2]将本发明害虫防治剂用溶剂例如水等稀释,然后将该稀释液喷到害虫或害虫栖息的场所的方法。
在该情况中,将通常配制的本发明害虫防治剂例如可乳化浓缩物、可湿性粉剂、可流动制剂、微囊等稀释至0.1-10000ppm浓度。
[3]将本发明害虫防治剂在害虫栖息的场所加热,使活性成分挥发的方法。
在该情况下,本发明化合物的施用量和施用浓度均可以根据本发明害虫防治剂的形式、施用时间、施用场所、施用方法、害虫种类、损害状况等适当确定。
可将本发明害虫防治剂与其它杀虫剂、杀线虫剂、土壤害虫防治剂、杀真菌剂、除草剂、植物生长调节剂、驱避剂、增效剂、肥料或土壤改良剂混合,或与它们一起使用。
此类杀虫剂和杀螨剂活性成分的实例包括有机磷化合物,例如杀螟松、倍硫磷、二嗪农、毒死蜱、乙酰甲胺磷、杀扑磷、乙拌磷、DDVP、甲丙硫磷、杀螟腈、蔬果磷、乐果、稻丰散、马拉硫磷、敌百虫、谷硫磷、久效磷、乙硫磷等;
氨基甲酸酯化合物例如BPMC、丙硫克百威、残杀威、丁硫克百威、胺甲萘、灭多威、乙硫苯威、涕灭威、杀线威、排螨净等;
拟除虫菊酯化合物例如醚菊酯、氰戊菊酯、顺式氰戊菊酯、甲氰菊酯、氯氰菊酯、氯菊酯、三氟氯氰菊酯、溴氰菊酯、乙氰菊酯、fulvalinate、联苯菊酯、2-甲基-2-(4-溴二氟甲氧基苯基)丙基(3-苯氧基苄基)醚、四溴菊酸、氟硅菊酯、d-苯醚菊酯、苯醚氰菊酯、d-灭虫菊、氰丙菊酯、氟氯菊酯、七氟菊酯、四氟苯菊酯、似虫菊、丙烯除虫菊、右旋炔丙菊酯、右旋炔丙菊酯、烯炔菊酯、2,2,3,3-四甲基环丙烷甲酸5-(2-丙炔基)糠基酯等;
硝基咪唑烷衍生物:N-氰基脒衍生物例如啶虫咪等;氯代烃化合物例如硫丹、γ-BHC、1,1-二(氯苯基)-2,2,2-三氯乙醇等;苯甲酰基苯脲化合物例如定虫隆、伏虫隆、氟虫脲等;苯基吡唑化合物;噁虫酮;溴螨酯;四氯杀螨砜;灭螨猛;蟽螨酮;唑螨酯;杀螨胺;吡螨胺;多萘菌素复合物[四抗菌素、二活菌素、三活菌素];嘧螨醚;密灭汀;阿巴克定;伊维菌素;和印楝素。
驱避剂的实例包括3,4-蒈烷二醇、N,N-二乙基-间甲苯甲酰胺、1-甲基丙基2-(2-羟基乙基)-1-哌啶甲酸酯、对-薄荷烷-3,8-二醇、植物精油例如牛膝草油等。
增效剂的实例包括二-(2,3,3,3-四氯丙基)醚(S-421)、N-(2-乙基己基)双环[2.2.1]庚-5-烯-2,3-二甲酰亚胺(MGK-264)和A-[2-(2-丁氧基乙氧基)乙氧基]-4,5-亚甲二氧基-2-丙基甲苯(胡椒基丁醚)。
在下文中,通过制备实施例、制剂实施例和测试实施例更详细地进一步说明本发明,但本发明不限于这些实施例。
首先,显示本发明的制备实施例。
制备实施例1
在氮气氛下,将0.59g N,N-二环己基碳二亚胺加入0.55g 4-甲基-2,3,5,6-四氟苄醇、0.51g(1R)-反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸、0.10g 4-二甲基氨基吡啶和7ml无水二氯甲烷的混合物中,将混合物在室温下搅拌3小时。然后,将反应混合物过滤,将滤液减压浓缩。得到的残渣进行硅胶柱层析,得到0.72g下式代表的(1R)-反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-甲基-2,3,5,6-四氟苄酯:
(关于双键的异构体比例:Z/E=约2/1)(下文中称为本发明化合物(1))。
1H-NMR(CDCl3,TMS)δ(ppm):1.21(s,3H,Z+E异构体),1.32(s,3H,Z+E异构体),1.71(t,1H,Z+E异构体),1.95(s,3H,Z+E异构体),2.19(m,1/3H,E异构体),2.29(s,3H,Z+E异构体),2.45(m,2/3H,Z异构体),5.24(s,2H,Z+E异构体),5.78(d,2/3H,Z异构体),6.00(d,1/3H,E异构体)
制备实施例2
在氮气氛下,将0.49g N,N-二环己基碳二亚胺加入0.50g 4-甲氧基-2,3,5,6-四氟苄醇、0.43g(1R)-反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸、0.087g 4-二甲基氨基吡啶和7ml无水二氯甲烷的混合物中,将混合物在室温下搅拌3小时。然后,将反应混合物过滤,将滤液减压浓缩。得到的残渣进行硅胶柱层析,得到0.62g下式代表的(1R)反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-甲氧基-2,3,5,6-四氟苄酯:
(关于双键的异构体比例:Z/E=约2/1)(下文中称为本发明化合物(2))。
1H-NMR(CDCl3,TMS)δ(ppm):1.21(s,3H,Z+E异构体),1.31(s,3H,Z+E异构体),1.72(t,1H,Z+E异构体),1.96(s,3H,Z+E异构体),2.19(m,1/3H,E异构体),2.46(m,2/3H,Z异构体),4.11(s,3H,Z+E异构体),5.20(s,2H,Z+E异构体),5.77(d,2/3H,Z异构体),6.00(d,1/3H,E异构体)
制备实施例3
在氮气氛下,将0.23g 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐加入0.20g 4-烯丙基-2,3,5,6-四氟苄醇、0.16g(1R)-反式-3-(2-氰基-1-丙烯基(propeny))-2,2-二甲基环丙烷甲酸、0.05g 4-二甲基氨基吡啶和4ml无水氯仿的混合物中,将混合物在室温下搅拌3小时。然后,将反应混合物倾入冰水中,然后用乙酸乙酯萃取两次。将乙酸乙酯层合并,用饱和氯化钠水溶液洗涤,用无水硫酸钠干燥,减压浓缩。得到的残渣进行硅胶柱层析,得到0.32g下式代表的(1R)-反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-烯丙基-2,3,5,6-四氟苄酯:
(关于双键的异构体比例:Z/E=约2/1)(下文中称为本发明化合物(3))。
1H-NMR(CDCl3,TMS)δ(ppm):1.23(s,3H,Z+E异构体),1.35(s,3H,Z+E异构体),1.71(t,1H,Z+E异构体),1.97(s,3H,Z+E异构体),2.20(m,1/3H,E异构体),2.46(m,2/3H,Z异构体),3.49(m,2H,Z+E异构体),5.10(m,2H,Z+E异构体),5.23(s,2H,Z+E异构体),5.79(d,2/3H,Z异构体),5.88(m,1H,Z+E异构体),6.00(d,1/3H,E异构体)
然后,显示制剂实施例。所有“份数”均按重量计。
准备实施例1
将本发明化合物(1)-(3)各20份溶于65份二甲苯,向其中加入15份Sorpol 3005X(Toho Chemical Industry Co.,LTD.的注册商标),将得到的混合物搅拌,充分混合,得到可乳化浓缩物。
制剂实施例2
向本发明化合物(1)-(3)各40份中加入5份Sorpol 3005X,将得到的混合物充分混合。向混合物中加入32份CARPLEX#80(合成水合二氧化硅,Shionogi&Co.,Ltd.的注册商标)和23份300目硅藻土。将得到的混合物搅拌,用果汁搅拌器混合,得到可湿性粉剂。
制剂实施例3
将本发明化合物(1)-(3)各1.5份、1份TOKUSIL GUN(合成水合二氧化硅,由Tokuyama Corp.制备)、2份REAX 85A(木质素磺酸钠,由Westvaco chemicals制备)、30份膨润土FUJI(膨润土,由HOJUN Co.,Ltd.制备)和65.5份SHOKOZAN A粘土(高岭土,由ShokozanKogyosho Co.制备)研磨,充分混合。向其中加入水,将混合物充分揉捏,用挤出制粒机制粒,干燥,得到1.5%颗粒。
制剂实施例4
将本发明化合物(1)-(3)各10份、10份苯基二甲苯基乙烷和0.5份SUMIDUR L-75(甲苯二异氰酸酯,由Sumika Bayer Urethane Co.,Ltd制备)混合。将得到的混合物加入20份10%阿拉伯胶水溶液中,然后用均匀混合器搅拌,得到平均粒径20μm的乳液。向乳液中加入2份乙二醇,将混合物在60℃温水浴中再搅拌24小时,得到微囊浆状物。将0.2份黄原胶和1.0份VEEGUM R(硅酸铝镁,由SanyoChemical Industries,Ltd.制备)分别分散到56.3份离子交换水中,得到较稠的溶液。然后,将42.5份微囊浆状物和57.5份较稠溶液混合,得到微囊化制剂。
制剂实施例5
将本发明化合物(1)-(3)各10份和10份苯基二甲苯基乙烷混合,将混合物加入20份10%聚乙二醇水溶液中,然后用均匀混合器搅拌,得到平均粒径3μm的乳液。将0.2份黄原胶和1.0份VEEGUM R(硅酸铝镁,由Sanyo.Chemical Industries,Ltd.制备)分别分散到58.8份离子交换水中,得到较稠溶液。然后,将40份乳液和60份较稠溶液混合,得到可流动制剂。
制剂实施例6
向本发明化合物(1)-(3)各5份中加入3份CARPLEX#80(合成水合二氧化硅细粉,Shionogi&Co.,Ltd.的注册商标)、0.3份PAP(磷酸单异丙酯和磷酸二异丙酯的混合物)和91.7份滑石粉(300目),将混合物搅拌,用果汁混合器混合,得到粉剂。
制剂实施例7
将本发明化合物(1)-(3)各0.1份溶于10份二氯甲烷,将溶液与89.9份脱臭煤油混合,得到油溶液。
制剂实施例8
将本发明化合物(1)-(3)各1份、5份二氯甲烷和34份脱臭煤油混合,溶解,填充至气雾剂容器。将阀部件连接后,压力下,将60份抛射剂(液化石油气)通过阀部件填充,得到油性气雾剂。
制剂实施例9
将通过混合和溶解本发明化合物(1)-(3)各0.6份、5份二甲苯、3.4份脱臭煤油和1份ATMOS 300(乳化剂,Atlas Chemical Co.的注册商标)和50份水得到的溶液填充至气雾剂容器,在压力下,将40份抛射剂(液化石油气)通过阀部件填充,得到水性气雾剂。
制剂实施例10
将本发明化合物(1)-(3)各0.3g溶于20ml丙酮,将溶液和99.7g盘状物的基质材料(通过以4∶3∶3的比例将Tabu粉末、除虫菊和木粉混合得到)均匀的搅拌并混合,向其中加入100ml水,将混合物充分揉捏,模制,干燥,得到杀虫剂盘状物。
制剂实施例11
将丙酮加入本发明化合物(1)-(3)各0.8g和0.4g胡椒基丁醚中,将它们溶解,并将总体积调至10ml。用0.5ml该溶液,均匀浸渍厚度为0.3cm的2.5cm×1.5cm电热杀虫用垫子的基质材料(将棉绒和纸浆混合物的原纤维以板的形状硬化),得到电热杀虫用垫子。
制剂实施例12
将本发明化合物(1)-(3)各3份溶于97份脱臭煤油,得到溶液,将溶液置于由聚氯乙烯制成的容器中,将具有可被加热器加热的上端部分的吸收性芯(通过将无机粉末与粘合剂一起固化,并将其煅烧得到)插入,得到用于吸收性芯型电热烟熏装置的一部分。
制剂实施例13
将本发明化合物(1)-(3)各100mg溶于适量丙酮中,将厚度为1.2cm的4.0cm×4.0cm多孔性陶瓷板用溶液浸渍,得到加热薰剂。
制剂实施例14
将本发明化合物(1)-(3)各100μg溶于适量丙酮中,将溶液均匀涂覆在厚度为0.3mm的2cm×2cm滤器上,将丙酮空气干燥,得到在室温下使用的挥发性制剂。
然后,通过测试实施例证明本发明化合物为有效的害虫防治剂活性成分。
测试实施例1
将在以上制备实施例中制备的本发明化合物(1)-(3)各0.025份溶于10份二氯甲烷中,将溶液与89.975份脱臭煤油混合,制备0.025%油溶液。
将成虫家蝇(5只雄性和5只雌性,总数10只)在各边为70cm的立方体室中释放,在8.8×104Pa压力下,用喷枪将0.7ml 0.025%以上制备的本发明化合物的油溶液通过室侧面上的小窗喷到该室中。喷射2分钟后,计数击倒的家蝇数目(重复2次)。
另外,用下式代表的(1R)-反式-3-(2-甲基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-甲基-2,3,5,6-四氟苄酯:
(EP0926129A1中所述化合物;下文中称为对比化合物(1));下式代表的(1R)-反式-3-(2-甲基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-甲氧基-2,3,5,6-四氟苄酯:
(美国专利4405640中所述化合物;下文中称为对比化合物(2));和下式代表的(1R)-反式-3-(2-甲基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-烯丙基-2,3,5,6-四氟苄酯:
(美国专利4405640中所述化合物;下文中称为对比化合物(3))作对照,代替本发明化合物(1)-(3),进行与上述相同的试验。
结果见表1所示。
表1
试验化合物 | 击倒的家蝇数目 |
本发明化合物(1) | 10 |
本发明化合物(2) | 10 |
本发明化合物(3) | 9 |
对比化合物(1) | 0 |
对比化合物(2) | 0 |
对比化合物(3) | 0 |
测试实施例2
将在以上制备实施例中制备的本发明化合物(1)-(3)各0.00625份溶于10份二氯甲烷中,将溶液与89.99375份脱臭煤油混合,制备0.00625%油溶液。
将10只普通雌性蚊子(淡色库蚊(Culex pipens pallens))在各边为70cm的立方体室中释放,在8.8×104Pa压力下,用喷枪将0.7ml0.00625%以上制备的本发明化合物的油溶液通过室侧面上的小窗喷到该室中。10分钟后,将普通雌性蚊子回收在清洁杯(底部直径8.2cm)中,该杯子具有含0.5%糖水溶液的棉絮,将其放置至次日。24小时后,计数死亡的蚊子数目,计算死亡率(重复2次)。
另外,用(1R)-反式-3-(2-氰基-1-丙烯基)-2,2-二甲基环丙烷甲酸4-甲氧基甲基-2,3,5,6-四氟苄酯(关于双键的异构体比例:Z/E=约2/1;美国专利6908945B2中所述化合物;下文称为对比化合物(4))作对照,代替本发明化合物(1)-(3),进行与上述相同的试验。
结果见表2所示。
表2
试验化合物 | 死亡率(%) |
本发明化合物(1) | 95 |
本发明化合物(2) | 100 |
本发明化合物(3) | 70 |
对比化合物(4) | 16 |
工业实用性
因为本发明化合物具有优良的害虫防治效力,所以它可用作害虫防治剂的活性成分。
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