CN104185628B - 芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途 - Google Patents
芳基烷氧基嘧啶衍生物、含有芳基烷氧基嘧啶衍生物作为活性成分的农业和园艺用杀虫剂、以及它们的用途 Download PDFInfo
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- CN104185628B CN104185628B CN201380017729.3A CN201380017729A CN104185628B CN 104185628 B CN104185628 B CN 104185628B CN 201380017729 A CN201380017729 A CN 201380017729A CN 104185628 B CN104185628 B CN 104185628B
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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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- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
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- 241000701451 unidentified granulovirus Species 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-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
- 230000037303 wrinkles Effects 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
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- 229960001763 zinc sulfate Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
由式(I)表示的芳基烷氧基嘧啶衍生物或其盐以及含有所述化合物作为活性成分的农业园艺用杀虫剂及其使用方法,其中R1是烷基、环烷基、烯基、炔基、卤代烷基、卤代烯基、卤代炔基、烷氧基烷基、二氧杂环戊烷基等;R2和R3各自是氢原子、烷基等;X是烷基、环烷基、烯基、炔基、卤代烷基、卤代烯基、卤代炔基、三烷基甲硅烷基等;Y是CH或氮原子;q是1‑3的整数;m是0‑5的整数;且n是0或1。
Description
技术领域
本发明涉及含有芳基烷氧基嘧啶衍生物或其盐作为活性成分的农业园艺用杀虫剂及其使用方法。
背景技术
专利文献1提示,其中嘧啶环的4-位被芳基烷氧基取代的衍生物具有抗真菌或杀虫活性。另外,专利文献2描述,特定种类的嘧啶衍生物可用作药物产品。但是,其不含有关于杀虫活性的描述。
[文献列表]
[专利文献]
专利文献1: JP-A-08-283246
专利文献2: WO1996/011902。
发明内容
本发明要解决的问题
在农业和园艺领域的作物生产中,由害虫引起的损害依然严重,并且由于对现有药剂具有抗性的害虫的产生等,因而期望开发出新颖的农业园艺用杀虫剂和杀螨剂。由于高龄农业就业人口的数目的增加而需要各种省力的施用方法,还需要创造具有适合于该施用方法的性质的农业园艺用杀虫剂和杀螨剂。
解决问题的方式
本发明的发明人为了开发出新颖的农业园艺用杀虫剂而进行了深入的研究,并已经发现,本发明的由式(I)表示的芳基烷氧基嘧啶衍生物或其盐可用作农业园艺用杀虫剂,这导致本发明的完成。
因此,本发明涉及
[1]由式(I)表示的芳基烷氧基嘧啶衍生物或其盐:
其中R1是
(a1)卤素原子;
(a2)甲酰基;
(a3)氰基;
(a4) (C1-C8)烷基;
(a5) (C3-C8)环烷基;
(a6) (C2-C8)烯基;
(a7) (C2-C8)炔基;
(a8)卤代(C1-C8)烷基;
(a9)卤代(C3-C8)环烷基;
(a10)卤代(C2-C8)烯基;
(a11)卤代(C2-C8)炔基;
(a12) (C1-C8)烷氧基(C1-C8)烷基;
(a13) (C3-C8)环烷基(C1-C8)烷基;
(a14) (C1-C8)烷氧基卤代(C1-C8)烷基;
(a15) (C3-C8)环烷基卤代(C1-C8)烷基;
(a16) (C1-C8)烷硫基(C1-C8)烷基;
(a17) (C1-C8)烷基亚磺酰基(C1-C8)烷基;
(a18) (C1-C8)烷基磺酰基(C1-C8)烷基;
(a19)卤代(C1-C8)烷氧基(C1-C8)烷基;
(a20)卤代(C3-C8)环烷基(C1-C8)烷基;
(a21)卤代(C1-C8)烷硫基(C1-C8)烷基;
(a22)卤代(C1-C8)烷基亚磺酰基(C1-C8)烷基;
(a23)卤代(C1-C8)烷基磺酰基(C1-C8)烷基;
(a24)卤代(C1-C8)烷氧基卤代(C1-C8)烷基;
(a25)氰基(C1-C8)烷基;
(a26)硝基(C1-C8)烷基;
(a27) R4(R5)N(C1-C8)烷基,其中R4和R5可以相同或不同,且各自为(i)氢原子,(ii) (C1-C6)烷基,(iii) (C3-C6)环烷基,(iv) (C2-C6)烯基,(v) (C2-C6)炔基,(vi) (C3-C6)环烷基(C1-C6)烷基,(vii)卤代(C1-C6)烷基,(viii)卤代(C3-C6)环烷基,(ix)卤代(C2-C6)烯基,(x)卤代(C2-C6)炔基,(xi)卤代(C3-C6)环烷基(C1-C6)烷基,(xii) (C1-C6)烷基磺酰基,(xiii) (C1-C6)烷基羰基,(xiv)卤代(C1-C6)烷基羰基,(xv) (C1-C6)烷氧基羰基,(xvi) (C3-C6)环烷基羰基,(xvii)苯基,(xviii)苯基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b) (C1-C6)烷基、(c)卤代(C1-C6)烷基、(d) (C1-C6)烷氧基、(e)卤代(C1-C6)烷氧基和(f)苯氧基,(xix)苯氧基苯基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b) (C1-C6)烷基、(c)卤代(C1-C6)烷基、(d)(C1-C6)烷氧基和(e)卤代(C1-C6)烷氧基,(xx)羟基(C1-C8)烷基,(xxi)苯基(C1-C6)烷基,(xxii)苯基(C1-C6)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b) (C1-C6)烷基、(c)卤代(C1-C6)烷基、(d) (C1-C6)烷氧基、(e)卤代(C1-C6)烷氧基和(f)苯氧基,或(xxiii)苯氧基苯基(C1-C6)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b) (C1-C6)烷基、(c)卤代(C1-C6)烷基、(d) (C1-C6)烷氧基和(e)卤代(C1-C6)烷氧基;
(a28) (R4)OC(C1-C8)烷基,其中R4如上面所定义;
(a29) (R4)O2C(C1-C8)烷基,其中R4如上面所定义;
(a30) R4(R5)NCO(C1-C8)烷基,其中R4和R5如上面所定义;
(a31)芳基;
(a32)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)苯氧基;
(a33)芳基(C1-C8)烷基;
(a34)芳基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r)(C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a35)芳基羰基;
(a36)芳基羰基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a37)芳硫基(C1-C8)烷基;
(a38)芳硫基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a39)芳基亚磺酰基(C1-C8)烷基;
(a40)芳基亚磺酰基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a41)芳基磺酰基(C1-C8)烷基;
(a42)芳基磺酰基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C8)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a43) (C1-C8)烷基羰基;
(a44) (C3-C8)环烷基羰基;
(a45) (C1-C8)烷氧基羰基;
(a46) R4(R5)N羰基,其中R4和R5如上面所定义;
(a47) (C1-C8)烷氧基(C1-C8)烷氧基(C1-C8)烷基;
(a48) (C1-C8)烷氧基羰基(C1-C8)烷基;
(a49)杂环基团;
(a50)杂环基团,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t)苯基、(u)氧代基团和(v) (C1-C6)烷氧基羰基(C1-C6)烷基;
(a51)杂环基(C1-C8)烷基;
(a52)杂环基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C8)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a53)杂环基(C3-C8)环烷基;
(a54)杂环基(C3-C8)环烷基,其在杂环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a55)三(C1-C8)烷基甲硅烷基(C1-C8)烷基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a56) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(a57)氧杂环丙基;
(a58)四氢吡喃基氧基(C1-C8)烷基;
(a59)四氢呋喃基氧基(C1-C8)烷基;
(a60)四氢吡喃基羰基;
(a61)甲酰氧基(C1-C8)烷基;
(a62) (C1-C8)烷硫基(C1-C8)烷基羰基;
(a63)杂环基羰基;
(a64)杂环基羰基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a65)羟基(C1-C8)烷基;
(a66)芳氧基(C1-C8)烷基;
(a67)芳氧基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a68) (C1-C8)烷硫基(C1-C8)烷氧基(C1-C8)烷基;
(a69) (C1-C8)烷基亚磺酰基(C1-C8)烷氧基(C1-C8)烷基;
(a70) ((C1-C8)烷氧基)((C3-C8)环烷基)(C1-C8)烷基;
(a71) R4CO(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a72) R4CO2(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a73) R4SO2(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a74) R4(R5)NCO2(C1-C8)烷基,其中R4和R5如上面所定义;
(a75) (R4(R5)N)((C3-C8)环烷基)(C1-C8)烷基,其中R4和R5如上面所定义;
(a76) ((C1-C8)烷硫基)((C3-C8)环烷基)(C1-C8)烷基;
(a77) ((C1-C8)烷基亚磺酰基)((C3-C8)环烷基)(C1-C8)烷基;
(a78) ((C1-C8)烷基磺酰基)((C3-C8)环烷基)(C1-C8)烷基;
(a79) (杂环基)((C3-C8)环烷基)(C1-C8)烷基;
(a80) (杂环基)((C3-C8)环烷基)(C1-C8)烷基,其在杂环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a81) (杂环基)((C1-C8)烷氧基)(C1-C8)烷基;
(a82) (杂环基)((C1-C8)烷氧基)(C1-C8)烷基,其在杂环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a83)二(C1-C8)烷氧基(C1-C8)烷基,其中所述二(C1-C8)烷氧基的烷氧基可以相同或不同;
(a84)二(C1-C8)烷硫基(C1-C8)烷基,其中所述二(C1-C8)烷硫基的烷基可以相同或不同;
(a85)三(C1-C8)烷基甲硅烷基氧基(C1-C8)烷基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a86)羧基;
(a87)芳氧基羰基;
(a88) C(R4)=NOSO2R5基团,其中R4和R5如上面所定义;
(a89)杂环基亚氨基(C1-C8)烷基;
(a90)三(C1-C8)烷基甲硅烷基(C2-C8)炔基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a91) (C1-C8)烷氧基(C2-C8)炔基;
(a92)羟基(C2-C8)炔基;
(a93) (羟基)((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基;
(a94)二羟基(C1-C8)烷基;
(a95) (羟基)((C1-C8)烷氧基)(C1-C8)烷基;
(a96)二(C1-C8)烷基磺酰氧基(C1-C8)烷基,其中所述二(C1-C8)烷基磺酰氧基的烷基可以相同或不同;
(a97)二((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基,其中所述二((C1-C8)烷氧基(C1-C8)烷氧基的烷氧基可以相同或不同;
(a98)二(C1-C8)烷氧基羰基(C2-C8)烯基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a99) (C1-C8)烷氧基羰基(氰基)(C2-C8)烯基;
(a100) ((C1-C8)烷氧基(C1-C8)烷氧基)(羟基)(C1-C8)烷基;
(a101)二氰基(C2-C8)烯基;
(a102) (C3-C8)亚环烷基(C1-C8)烷基;
(a103) (C3-C8)环烷基(羟基)(C1-C8)烷基;
(a104) (C3-C8)环烷基((C1-C8)烷氧基)(C1-C8)烷基;
(a105)杂环基(C2-C8)烯基;
(a106)杂环基(C2-C8)烯基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a107)卤代(C1-C8)烷基碳酰氧基(C2-C8)烯基;
(a108) (C3-C8)环烷基(卤代(C1-C8)烷基碳酰氧基)(C1-C8)烷基;
(a109) (C1-C8)烷氧基羰基(羟基)(C1-C8)烷基;
(a110)羧基(羟基)(C1-C8)烷基;
(a111)二(C1-C8)烷氧基羰基(C3-C8)环烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a112)二(C1-C8)烷氧基羰基(C1-C8)烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a113) (C1-C8)烷基羰基(C2-C8)烯基;
(a114)羟基卤代(C1-C8)烷基;
(a115)二羟基卤代(C1-C8)烷基;
(a116) (C1-C8)烷氧基羰基(C3-C8)环烷基;
(a117)氰基(C3-C8)环烷基;
(a118) (C1-C8)烷氧基羰基(C2-C8)烯基;
(a119)氰基(C2-C8)烯基;
(a120) ((C1-C8)烷氧基)(羟基)卤代(C1-C8)烷基;
(a121) R4(R5)N(C1-C8)烷基(R5)N羰基,其中R4和R5如上面所定义;
(a122) R4(R5)NCO(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a123)三(C1-C8)烷基甲硅烷基(C2-C8)炔基(C2-C8)烯基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;或
(a124)以下结构式Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q9、Q10、Q11、Q12、Q13、Q14、Q15、Q16、Q17、Q18、Q19、Q20、Q21、Q22、Q23、Q24、Q25、Q26、Q27、Q28或Q29
其中R6、R7和R8可以相同或不同,且各自为氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基(C1-C6)烷基、卤代(C1-C6)烷基、卤代(C3-C6)环烷基、卤代(C2-C6)烯基、卤代(C2-C6)炔基、卤代(C3-C6)环烷基(C1-C6)烷基、(C1-C6)烷基碳酰氧基(C1-C6)烷基、(C1-C6)烷氧基(C1-C6)烷基、羟基(C1-C6)烷基、(C2-C6)烯基氧基(C1-C6)烷基、苯氧基(C1-C6)烷基、(C1-C6)烷基磺酰基(C1-C6)烷基、(C1-C6)烷基磺酰氧基(C1-C6)烷基、卤素原子、苯基、苯基(C1-C6)烷基或(C1-C6)烷基羰基,
R9是氰基、卤代(C1-C6)烷基或卤代(C1-C6)烷基羰基,
p是0-5的整数,且Z1和Z2可以相同或不同,且各自为碳原子、氧原子、S、SO、SO2或NR6,其中R6如上面所定义,或当p是2时,相邻的2个R7可以键合以形成3-8元脂族环。
R2和R3可以相同或不同,且各自为
(b1)氢原子;
(b2) (C1-C8)烷基;
(b3) (C3-C8)环烷基;
(b4) (C2-C8)烯基;
(b5) (C2-C8)炔基;
(b6)卤代(C1-C8)烷基;
(b7)卤代(C3-C8)环烷基;
(b8)卤代(C2-C8)烯基;
(b9)卤代(C2-C8)炔基;
(b10) (C3-C8)环烷基(C1-C8)烷基;
(b11) (C1-C8)烷氧基(C1-C8)烷基;
(b12) (C1-C8)烷硫基(C1-C8)烷基;或
(b13) (C1-C8)烷氧基羰基,
q是1-3的整数。
X可以相同或不同,且各自为
(c1)氢原子;
(c2)卤素原子;
(c3)羟基;
(c4)氰基;
(c5)硝基;
(c6) N(R4)(R5)基团,其中R4和R5如上面所定义;
(c7) N(R4)CO(R5)基团,其中R4和R5如上面所定义;
(c8) N(R4)SO2(R5)基团,其中R4和R5如上面所定义;
(c9) N(R4)CO2(R5)基团,其中R4和R5如上面所定义;
(c10) CO(R4)基团,其中R4如上面所定义;
(c11) CO2(R4)基团,其中R4如上面所定义;
(c12) CON(R4)(R5)基团,其中R4和R5如上面所定义;
(c13) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c14) (C1-C8)烷基;
(c15) (C2-C8)烯基;
(c16) (C2-C8)炔基;
(c17) (C3-C8)环烷基;
(c18)卤代(C1-C8)烷基;
(c19)卤代(C2-C8)烯基;
(c20)卤代(C2-C8)炔基;
(c21)卤代(C3-C8)环烷基;
(c22)三(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c23)三(C1-C8)烷基甲硅烷基(C1-C8)烷基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(c24) (C3-C8)环烷基(C1-C8)烷基;
(c25)卤代(C3-C8)环烷基(C1-C8)烷基;
(c26) (C3-C8)环烷基(C3-C8)环烷基;
(c27) (C1-C8)烷氧基;
(c28) (C2-C8)烯基氧基;
(c29) (C2-C8)炔基氧基;
(c30) (C3-C8)环烷基氧基(所述环烷基任选地与苯环稠合);
(c31)卤代(C1-C8)烷氧基;
(c32)卤代(C2-C8)烯基氧基;
(c33)卤代(C2-C8)炔基氧基;
(c34)卤代(C3-C8)环烷基氧基(所述环烷基任选地与苯环稠合);
(c35) (C3-C8)环烷基(C1-C8)烷氧基;
(c36)卤代(C3-C8)环烷基(C1-C8)烷氧基;
(c37) (C1-C8)烷氧基(C1-C8)烷基;
(c38)卤代(C1-C8)烷氧基(C1-C8)烷氧基;
(c39) (C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c40)卤代(C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c41)巯基;
(c42) (C1-C8)烷硫基;
(c43) (C2-C8)烯基硫基;
(c44) (C2-C8)炔基硫基;
(c45) (C3-C8)环烷硫基;
(c46)卤代(C1-C8)烷硫基;
(c47)卤代(C2-C8)烯基硫基;
(c48)卤代(C2-C8)炔基硫基;
(c49)卤代(C3-C8)环烷硫基;
(c50) (C3-C8)环烷基(C1-C8)烷硫基;
(c51)卤代(C3-C8)环烷基(C1-C8)烷硫基;
(c52) (C1-C8)烷氧基(C1-C8)烷硫基;
(c53)卤代(C1-C8)烷氧基(C1-C8)烷硫基;
(c54) (C1-C8)烷氧基卤代(C1-C8)烷硫基;
(c55)卤代(C1-C8)烷氧基卤代(C1-C8)烷硫基;
(c56) (C1-C8)烷基亚磺酰基;
(c57) (C2-C8)烯基亚磺酰基;
(c58) (C2-C8)炔基亚磺酰基;
(c59) (C3-C8)环烷基亚磺酰基;
(c60)卤代(C1-C8)烷基亚磺酰基;
(c61)卤代(C2-C8)烯基亚磺酰基;
(c62)卤代(C2-C8)炔基亚磺酰基;
(c63)卤代(C3-C8)环烷基亚磺酰基;
(c64) (C3-C8)环烷基(C1-C8)烷基亚磺酰基;
(c65)卤代(C3-C8)环烷基(C1-C8)烷基亚磺酰基;
(c66) (C1-C8)烷基磺酰基;
(c67) (C2-C8)烯基磺酰基;
(c68) (C2-C8)炔基磺酰基;
(c69) (C3-C8)环烷基磺酰基;
(c70)卤代(C1-C8)烷基磺酰基;
(c71)卤代(C2-C8)烯基磺酰基;
(c72)卤代(C2-C8)炔基磺酰基;
(c73)卤代(C3-C8)环烷基磺酰基;
(c74) (C3-C8)环烷基(C1-C8)烷基磺酰基;
(c75)卤代(C3-C8)环烷基(C1-C8)烷基磺酰基;
(c76)芳基;
(c77)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c78)芳基(C1-C8)烷基;
(c79)芳基(C1-C6)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t)(C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c80)芳氧基;
(c81)芳氧基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c82)芳氧基(C1-C8)烷基;
(c83)芳氧基(C1-C6)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c84)芳硫基;
(c85)芳硫基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C2-C6)烷基亚磺酰基、(s)卤代(C2-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c86)卤代(C1-C8)亚烷基二氧基;
(c87) (C1-C8)烷氧基(C1-C8)烷氧基;
(c88) (C3-C8)亚烷基;
(c89) (C1-C8)烷基(C3-C8)亚烷基;
(c90)三(C1-C8)烷基甲硅烷基氧基,其中所述烷基可以相同或不同;
(c91)三(C1-C8)烷基甲硅烷基(C1-C8)烷氧基,其中所述烷基可以相同或不同;
(c92)二(C1-C8)烷基卤代(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c93)二(C1-C8)烷基(C1-C8)烷硫基(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c94)二(C1-C8)烷基羟基甲硅烷基,其中所述烷基可以相同或不同;
(c95)二(C1-C8)烷基氢化甲硅烷基,其中所述烷基可以相同或不同;
(c96)二(C1-C8)烷基苯基甲硅烷基,其中所述烷基可以相同或不同;
(c97) (C1-C8)烷硫基(C1-C8)烷氧基;
(c98) (C1-C8)烷基亚磺酰基(C1-C8)烷氧基;
(c99) (C1-C8)烷基磺酰基(C1-C8)烷氧基;
(c100) (C1-C8)烷氧基羰基(C1-C8)烷氧基;
(c101) (C1-C8)烷基羰基(C1-C8)烷氧基;
(c102)氰基(C1-C8)烷氧基;
(c103)芳基(C1-C8)烷氧基,其中所述烷氧基部分可以被卤代;
(c104)芳基(C1-C8)烷氧基,其中所述烷氧基部分可以被卤代,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C2-C6)烷基亚磺酰基、(s)卤代(C2-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c105)羟基(C1-C8)烷基;
(c106) (C1-C8)烷硫基(C1-C8)烷基羰基;
(c107) (C1-C8)烷硫基(C1-C8)烷基;
(c108)三(C1-C8)烷基甲硅烷基(C1-C8)烷硫基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(c109)三(C1-C8)烷基甲硅烷基(C1-C8)烷基亚磺酰基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(c110)三(C1-C8)烷基甲硅烷基(C1-C8)烷基磺酰基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(c111) R4(R5) N(C1-C8)烷基,其中R4和R5如上面所定义;
(c112)杂环基团;
(c113)杂环基团,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c114)杂环基氧基;
(c115)杂环基氧基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r)(C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c116)杂环基硫基;
(c117)杂环基硫基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r)(C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c118)杂环基亚磺酰基;
(c119)杂环基亚磺酰基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r)(C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c120)杂环基磺酰基;
(c121)杂环基磺酰基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r)(C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c122)杂环基(C1-C8)烷氧基;
(c123)杂环基(C1-C8)烷氧基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团;
(c124) (C1-C8)烷基(C3-C8)环烷基;
(c125)卤代(C1-C8)烷基(C3-C8)环烷基;
(c126) (C1-C8)烷基亚磺酰基(C1-C8)烷基;
(c127)二(C1-C8)烷基苄基甲硅烷基,其中所述烷基可以相同或不同;
(c128)杂环基(C1-C8)烷基;
(c129)杂环基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团,
(c130)杂环基氧基(C1-C8)烷基;或
(c131)杂环基氧基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t) (C2-C6)炔基、(u)三(C1-C6)烷基甲硅烷基(C1-C6)烷基(其中所述三(C1-C6)烷基甲硅烷基的烷基可以相同或不同)、(v)三(C1-C6)烷基甲硅烷基(C2-C6)炔基(其中所述烷基可以相同或不同)和(w)氧代基团,或
X可以与相邻的R2或R3一起形成(C132)二环,其中所述二环任选地具有相同的或不同的一个或多个取代基,所述取代基选自(a)卤素原子、(b) (C1-C6)烷基、(c)卤代(C1-C6)烷基、(d) (C1-C6)烷氧基、(e)卤代(C1-C6)烷氧基、(f) (C1-C6)烷硫基、(g)卤代(C1-C6)烷硫基、(h) (C1-C6)烷基亚磺酰基、(i)卤代(C1-C6)烷基亚磺酰基、(j) (C1-C6)烷基磺酰基和(k)卤代(C1-C6)烷基磺酰基;或者,
X可以与芳族环上的相邻X一起形成(C133)二环或(C134)稠合环,其中所述二环或稠合环任选地具有相同的或不同的一个或多个取代基,所述取代基选自(a)卤素原子、(b)(C1-C6)烷基、(c)卤代(C1-C6)烷基、(d) (C1-C6)烷氧基、(e)卤代(C1-C6)烷氧基、(f) (C1-C6)烷硫基、(g)卤代(C1-C6)烷硫基、(h) (C1-C6)烷基亚磺酰基、(i)卤代(C1-C6)烷基亚磺酰基、(j) (C1-C6)烷基磺酰基和(k)卤代(C1-C6)烷基磺酰基,
Y是CH或氮原子,m是0-5的整数,且n是0或1的整数;
[2]根据上述[1]所述的芳基烷氧基嘧啶衍生物或其盐,
其中Y、q、m和n如在上述[1]中定义,
R1是
(a1)卤素原子;
(a2)甲酰基;
(a3)氰基;
(a4) (C1-C8)烷基;
(a5) (C3-C8)环烷基;
(a6) (C2-C8)烯基;
(a7) (C2-C8)炔基;
(a8)卤代(C1-C8)烷基;
(a11)卤代(C2-C8)炔基;
(a12) (C1-C8)烷氧基(C1-C8)烷基;
(a13) (C3-C8)环烷基(C1-C8)烷基;
(a14) (C1-C8)烷氧基卤代(C1-C8)烷基;
(a16) (C1-C8)烷硫基(C1-C8)烷基;
(a17) (C1-C8)烷基亚磺酰基(C1-C8)烷基;
(a18) (C1-C8)烷基磺酰基(C1-C8)烷基;
(a27) R4(R5)N(C1-C8)烷基,其中R4和R5如在上述[1]中定义;
(a31)芳基;
(a32)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)苯氧基;
(a33)芳基(C1-C8)烷基;
(a37)芳硫基(C1-C8)烷基;
(a39)芳基亚磺酰基(C1-C8)烷基;
(a41)芳基磺酰基(C1-C8)烷基;
(a43) (C1-C8)烷基羰基;
(a45) (C1-C8)烷氧基羰基;
(a46) R4(R5)N羰基,其中R4和R5如上面所定义;
(a47) (C1-C8)烷氧基(C1-C8)烷氧基(C1-C8)烷基;
(a49)杂环基团;
(a50)杂环基团,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t)苯基、(u)氧代基团和(v) (C1-C6)烷氧基羰基(C1-C6)烷基;
(a51)杂环基(C1-C8)烷基;
(a56) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(a57)氧杂环丙基;
(a65)羟基(C1-C8)烷基;
(a66)芳氧基(C1-C8)烷基;
(a67)芳氧基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a81) (杂环基)((C1-C8)烷氧基)(C1-C8)烷基;
(a83)二(C1-C8)烷氧基(C1-C8)烷基,其中所述二(C1-C8)烷氧基的烷氧基可以相同或不同;
(a84)二(C1-C8)烷硫基(C1-C8)烷基,其中所述二(C1-C8)烷硫基的烷基可以相同或不同;
(a85)三(C1-C8)烷基甲硅烷基氧基(C1-C8)烷基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a86)羧基;
(a87)芳氧基羰基;
(a88) C(R4)=NOSO2R5基团,其中R4和R5如上面所定义;
(a89)杂环基亚氨基(C1-C8)烷基;
(a90)三(C1-C8)烷基甲硅烷基(C2-C8)炔基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a91) (C1-C8)烷氧基(C2-C8)炔基;
(a92)羟基(C2-C8)炔基;
(a93) (羟基)((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基;
(a94)二羟基(C1-C8)烷基;
(a95) (羟基)((C1-C8)烷氧基)(C1-C8)烷基;
(a96)二(C1-C8)烷基磺酰氧基(C1-C8)烷基,其中所述二(C1-C8)烷基磺酰氧基的烷基可以相同或不同;
(a97)二((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基,其中所述二((C1-C8)烷氧基(C1-C8)烷氧基的烷氧基可以相同或不同;
(a98)二(C1-C8)烷氧基羰基(C2-C8)烯基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a99) (C1-C8)烷氧基羰基(氰基)(C2-C8)烯基;
(a100) ((C1-C8)烷氧基(C1-C8)烷氧基)(羟基)(C1-C8)烷基;
(a101)二氰基(C2-C8)烯基;
(a102) (C3-C8)亚环烷基(C1-C8)烷基;
(a103) (C3-C8)环烷基(羟基)(C1-C8)烷基;
(a104) (C3-C8)环烷基((C1-C8)烷氧基)(C1-C8)烷基;
(a105)杂环基(C2-C8)烯基;
(a106)杂环基(C2-C8)烯基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a107)卤代(C1-C8)烷基碳酰氧基(C2-C8)烯基;
(a108) (C3-C8)环烷基(卤代(C1-C8)烷基碳酰氧基)(C1-C8)烷基;
(a109) (C1-C8)烷氧基羰基(羟基)(C1-C8)烷基;
(a110)羧基(羟基)(C1-C8)烷基;
(a111)二(C1-C8)烷氧基羰基(C3-C8)环烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a112)二(C1-C8)烷氧基羰基(C1-C8)烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a113) (C1-C8)烷基羰基(C2-C8)烯基;
(a114)羟基卤代(C1-C8)烷基;
(a115)二羟基卤代(C1-C8)烷基;
(a116) (C1-C8)烷氧基羰基(C3-C8)环烷基;
(a117)氰基(C3-C8)环烷基;
(a118) (C1-C8)烷氧基羰基(C2-C8)烯基;
(a119)氰基(C2-C8)烯基;
(a120) ((C1-C8)烷氧基)(羟基)卤代(C1-C8)烷基;
(a121) R4(R5)N(C1-C8)烷基(R5)N羰基,其中R4和R5如上面所定义;
(a122) R4(R5)NCO(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a123)三(C1-C8)烷基甲硅烷基(C2-C8)炔基(C2-C8)烯基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;或
(a124)结构式Q7、Q8、Q9、Q10、Q11、Q12、Q13、Q14、Q15、Q16、Q17、Q18、Q19、Q20、Q21、Q22、Q23、Q24、Q25、Q26、Q27、Q28或Q29,其中它们中的每个结构式和符号如在上述[1]中定义,
R2和R3可以相同或不同,且各自为
(b1)氢原子;或
(b6)卤代(C1-C8)烷基;
X可以相同或不同,且各自为
(c1)氢原子;
(c2)卤素原子;
(c4)氰基;
(c5)硝基;
(c10) CO(R4)基团,其中R4如上面所定义;
(c14) (C1-C8)烷基;
(c18)卤代(C1-C8)烷基;
(c22)三(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c27) (C1-C8)烷氧基;
(c31)卤代(C1-C8)烷氧基;
(c40)卤代(C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c42) (C1-C8)烷硫基;
(c46)卤代(C1-C8)烷硫基;
(c76)芳基;
(c77)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c80)芳氧基;或者
(c81)芳氧基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
[3]一种农业园艺用杀虫剂,其包含根据上述[1]或[2]所述的芳基烷氧基嘧啶衍生物或其盐作为活性成分;
[4]使用农业园艺用杀虫剂的方法,所述方法包括:用根据上述[1]或[2]所述的芳基烷氧基嘧啶衍生物或其盐处理植物或土壤;
[5]一种防治农业园艺害虫的方法,所述方法包括:用根据上述[1]或[2]所述的芳基烷氧基嘧啶衍生物或其盐处理植物或土壤;
[6]根据上述[1]或[2]所述的芳基烷氧基嘧啶衍生物或其盐作为农业园艺用杀虫剂的用途;
[7]根据上述[1]或[2]所述的芳基烷氧基嘧啶衍生物或其盐作为兽用杀虫剂的用途;
[8]由式(II)表示的芳基烷氧基嘧啶衍生物或其盐:
其中R1、R2、R3、X、Y、m和q如在上述[1]中定义,且
Hal是卤素原子;
等。
本发明的效果
本发明的芳基烷氧基嘧啶衍生物或其盐作为农业园艺用杀虫剂具有优异作用。另一方面,所述衍生物对寄生在宠物动物(诸如狗和猫)和家养动物(诸如牛、绵羊等)中的害虫显示出作用。
具体实施方式
在本发明的式(I)的芳基烷氧基嘧啶衍生物的定义中,
“卤素”是指“卤素原子”,且是氯原子、溴原子、碘原子或氟原子,
“(C1-C8)烷基”是,例如,具有1-8个碳原子的直链或支链烷基,诸如甲基、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、正庚基、2-庚基、3-庚基、2-甲基己基、3-甲基己基、4-甲基己基、异庚基、正辛基等,
“(C2-C8)烯基”是,例如,具有2-8个碳原子的直链或支链烯基,诸如乙烯基、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、庚烯基、辛烯基等,
“(C2-C8)炔基”是,例如,具有2-8个碳原子的直链或支链炔基,诸如乙炔基、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、庚炔基、辛炔基等。
“(C3-C8)环烷基”是,例如,具有3-8个碳原子的环状烷基,诸如环丙基、环丁基、环戊基、环己基、环庚基、环辛基等,
“(C3-C8)亚环烷基”是,例如,具有3-8个碳原子的环状亚烷基,诸如亚环丙基、亚环丁基、亚环戊基、亚环己基、亚环庚基、亚环辛基等,
“(C1-C8)烷氧基”是,例如,具有1-8个碳原子的直链或支链烷氧基,诸如甲氧基、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-甲基丁基氧基、正己氧基、异己氧基、1,1,2-三甲基丙氧基、正庚基氧基、正辛基氧基等,
“(C2-C8)烯基氧基”是,例如,具有2-8个碳原子的直链或支链烯基氧基,诸如丙烯基氧基、丁烯基氧基、戊烯基氧基、己烯基氧基、庚烯基氧基、辛烯基氧基等,
“(C2-C8)炔基氧基”是,例如,具有2-8个碳原子的直链或支链炔基氧基,诸如丙炔基氧基、丁炔基氧基、戊炔基氧基、己炔基氧基、庚炔基氧基、辛炔基氧基等。
“(C1-C8)烷硫基”的例子包括具有1-8个碳原子的直链或支链烷硫基,诸如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁基硫基、仲丁基硫基、叔丁基硫基、正戊基硫基、异戊基硫基、叔戊基硫基、新戊基硫基、2,3-二甲基丙基硫基、1-乙基丙基硫基、1-甲基丁基硫基、正己基硫基、异己基硫基、1,1,2-三甲基丙基硫基、正庚基硫基、正辛基硫基等,
“(C1-C8)烷基亚磺酰基”的例子包括具有1-8个碳原子的直链或支链烷基亚磺酰基,诸如甲基亚磺酰基、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、正庚基亚磺酰基、正辛基亚磺酰基等,
“(C1-C8)烷基磺酰基”的例子包括具有1-8个碳原子的直链或支链烷基磺酰基,诸如甲基磺酰基、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、正庚基磺酰基、正辛基磺酰基等。
“(C2-C8)烯基硫基”的例子包括具有2-8个碳原子的直链或支链烯基硫基,诸如丙烯基硫基、丁烯基硫基、戊烯基硫基、己烯基硫基、庚烯基硫基、辛烯基硫基等,
“(C2-C8)炔基硫基”的例子包括具有2-8个碳原子的直链或支链炔基硫基,诸如丙炔基硫基、丁炔基硫基、戊炔基硫基、己炔基硫基、庚炔基硫基、辛炔基硫基等。
“(C2-C8)烯基亚磺酰基”的例子包括具有1-8个碳原子的直链或支链烯基亚磺酰基,诸如丙烯基亚磺酰基、丁烯基亚磺酰基、戊烯基亚磺酰基、己烯基亚磺酰基、庚烯基亚磺酰基、辛烯基亚磺酰基等,
“(C2-C8)炔基亚磺酰基”的例子包括具有2-8个碳原子的直链或支链炔基亚磺酰基,诸如丙炔基亚磺酰基、丁炔基亚磺酰基、戊炔基亚磺酰基、己炔基亚磺酰基、庚炔基亚磺酰基、辛炔基亚磺酰基等。
“(C2-C8)烯基磺酰基”的例子包括具有2-8个碳原子的直链或支链烯基磺酰基,诸如丙烯基磺酰基、丁烯基磺酰基、戊烯基磺酰基、己烯基磺酰基、庚烯基磺酰基、辛烯基磺酰基等,
“(C2-C8)炔基磺酰基”的例子包括具有2-8个碳原子的直链或支链炔基磺酰基,诸如丙炔基磺酰基、丁炔基磺酰基、戊炔基磺酰基、己炔基磺酰基、庚炔基磺酰基、辛炔基磺酰基等。
“(C3-C8)环烷基氧基”是,例如,具有3-8个碳原子的环状烷氧基,诸如环丙氧基、环丁氧基、环戊氧基、环己氧基、环庚氧基、环辛氧基等,
“(C3-C8)环烷硫基”是,例如,具有3-8个碳原子的环状烷硫基,诸如环丙基硫基,环丁基硫基, 环戊基硫基, 环己基硫基, 环庚基硫基, 环辛基硫基等,
“(C3-C8)环烷基亚磺酰基”是,例如,具有3-8个碳原子的环状烷基亚磺酰基,诸如环丙基亚磺酰基、环丁基亚磺酰基、环戊基亚磺酰基、环己基亚磺酰基、环庚基亚磺酰基、环辛基亚磺酰基等,
“(C3-C8)环烷基磺酰基”是,例如,具有3-8个碳原子的环状烷基磺酰基,诸如环丙基磺酰基、环丁基磺酰基、环戊基磺酰基、环己基磺酰基、环庚基磺酰基、环辛基磺酰基等。
上述“(C1-C8)烷基”、“(C2-C8)烯基”、“(C2-C8)炔基”、“(C3-C8)环烷基”、“(C3-C8)环烷基氧基”、“(C1-C8)烷氧基”、“(C2-C8)烯基氧基”、“(C2-C8)炔基氧基”、“(C1-C8)烷硫基”、“(C1-C8)烷基亚磺酰基”、“(C1-C8)烷基磺酰基”、“(C2-C8)烯基硫基”、“(C2-C8)炔基硫基”、“(C2-C8)烯基亚磺酰基”、“(C2-C8)炔基亚磺酰基”、“(C2-C8)烯基磺酰基”、“(C2-C8)炔基磺酰基”、“(C3-C8)环烷基”、“(C1-C8)烷氧基”、“(C2-C8)烯基氧基”、“(C2-C8)炔基氧基”、“(C3-C8)环烷硫基”、“(C3-C8)环烷基亚磺酰基”和“(C3-C8)环烷基磺酰基”可以在可取代的位置被一个或多个卤素原子取代,且当被两个或多个卤素原子取代时,所述卤素原子可以相同或不同。
它们分别被称作“卤代(C1-C8)烷基”、“卤代(C2-C8)烯基”、“卤代(C2-C8)炔基”、“卤代(C3-C8)环烷基”、“卤代(C3-C8)环烷基氧基”、“卤代(C1-C8)烷氧基”、“卤代(C2-C8)烯基氧基”、“卤代(C2-C8)炔基氧基”、“卤代(C1-C8)烷硫基”、“卤代(C1-C8)烷基亚磺酰基”、“卤代(C1-C8)烷基磺酰基”、“卤代(C2-C8)烯基硫基”、“卤代(C2-C8)炔基硫基”、“卤代(C2-C8)烯基亚磺酰基”、“卤代(C2-C8)炔基亚磺酰基”、“卤代(C2-C8)烯基磺酰基”、“卤代(C2-C8)炔基磺酰基”、“卤代(C3-C8)环烷基”、“卤代(C1-C8)烷氧基”、“卤代(C2-C8)烯基氧基”、“卤代(C2-C8)炔基氧基”、“卤代(C3-C8)环烷硫基”、“卤代(C3-C8)环烷基亚磺酰基”和“卤代(C3-C8)环烷基磺酰基”。
“三(C1-C8)烷基甲硅烷基”是,例如,具有1-8个碳原子的直链或支链三烷基甲硅烷基,诸如三甲基甲硅烷基、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。在该情况下,所述三个烷基可以相同或不同。
二(C1-C8)烷基卤代(C1-C8)烷基甲硅烷基的例子包括氯甲基二甲基甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
二(C1-C8)烷基(C1-C8)烷硫基(C1-C8)烷基甲硅烷基的例子包括甲硫基甲基二甲基甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
二(C1-C8)烷基氢化甲硅烷基的例子包括二异丙基甲硅烷基、二甲基甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
二(C1-C8)烷基羟基甲硅烷基的例子包括二甲基羟基甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
二(C1-C8)烷基苯基甲硅烷基的例子包括二甲基(苯基)甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
二(C1-C8)烷基苄基甲硅烷基的例子包括二甲基(苄基)甲硅烷基等。在该情况下,所述两个烷基可以相同或不同。
“芳基”的例子包括具有的6-10的碳数的芳烃基,诸如苯基、1-萘基、2-萘基等。
“(C1-C8)”、“(C2-C8)”、“(C3-C8)”等的表述显示了各个取代基的碳原子数目的范围。此外,上述定义适用于这样的基团:其中上述取代基彼此键合。例如,“(C1-C8)烷氧基(C1-C8)烷基”是指,具有1-8的碳数的直链或支链烷氧基与具有1-8的碳数的直链或支链烷基键合。
另外,例如,“((C1-C8)烷氧基)((C3-C8)环烷基)(C1-C8)烷基”是指,具有1-8个碳原子的直链或支链烷氧基和具有3-8个碳原子的环状烷基与具有1-8个碳原子的直链或支链烷基键合。
当2个或更多个取代基键合时,每个取代基可以键合至相同碳原子或不同碳原子。例如,在“((C1-C8)烷氧基)((C3-C8)环烷基)(C1-C8)烷基”中,(C1-C8)烷氧基和(C3-C8)环烷基可以键合至(C1-C8)烷基的相同碳原子或不同碳原子。
“(C3-C8)亚烷基”、“(C1-C8)烷基(C3-C8)亚烷基”和“卤代(C1-C8)亚烷基二氧基”是可以与2个相邻的X基团一起形成的基团,且“(C3-C8)亚烷基”和“(C1-C8)烷基(C3-C8)亚烷基”的例子包括亚丙基、亚丁基、亚戊基、亚己基、1,1,4,4-四甲基亚丁基等,且“卤代(C1-C8)亚烷基二氧基”的例子包括二氟亚甲基二氧基、四氟亚乙基二氧基等。
由相邻的2个X形成的稠合环和二环或者由X与相邻的R2或R3一起形成的二环的例子包括:稠合环诸如四氢萘、萘、苯并二氧杂环戊烯、苯并二噁烷、茚满、吲哚、苯并呋喃、苯并噻吩、苯并咪唑、苯并噻唑、苯并噁唑等,和二环诸如四氢萘、萘、1,2,3,4-四氢-1,4-桥亚甲基萘、1,2,3,4-四氢-1,4-桥亚乙基萘等。
“杂环基团”和“杂环基”的例子包括:5或6元单环芳族杂环基团或3-6元单环非芳族杂环基团,其中的每一个含有1-4个选自氧原子、硫原子和氮原子的杂原子作为除了碳原子以外的成环原子;由所述单环芳族或非芳族杂环与苯环缩合而得到的稠合杂环基团;以及由所述单环芳族或非芳族杂环(杂环可以不同)缩合而得到的稠合杂环基团。
“芳族杂环基团”的例子包括
单环芳族杂环基团诸如呋喃基、噻吩基、吡啶基、嘧啶基、哒嗪基、吡嗪基、吡咯基、咪唑基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、三唑基、四唑基、三嗪基等;芳族稠合杂环基团诸如喹啉基、异喹啉基、喹唑啉基、喹握啉基、苯并呋喃基、苯并噻吩基、苯并噁唑基、苯并异噁唑基、苯并噻唑基、苯并咪唑基、苯并三唑基、吲哚基、吲唑基、吡咯并吡嗪基、咪唑并吡啶基、咪唑并吡嗪基、吡唑并吡啶基、吡唑并噻吩基、吡唑并三嗪基等。
“非芳族杂环基团”的例子包括
单环非芳族杂环基团诸如氧杂环丙基、硫杂丙环基、氮杂环丙基、氧杂环丁基、硫杂环丁基、氮杂环丁基、吡咯烷基、2-氧代吡咯烷-1-基、哌啶基、吗啉基、硫代吗啉基、哌嗪基、六亚甲基亚胺基(hexamethyleniminyl)、噁唑烷基、噻唑烷基、咪唑烷基、噁唑啉基、噻唑啉基、异噁唑啉基、咪唑啉基、二氧杂环戊烯基、二氧杂环戊烷基、二氢噁二唑基、2-氧代-1,3-噁唑烷-5-基、5-氧代-1,2,4-噁二唑啉-3-基、1,3-二氧杂环戊烷-2-基、1,3-二噁烷-2-基、1,3-二氧杂环庚烷-2-基、吡喃基、四氢吡喃基、噻喃基、四氢噻喃基、1-氧化四氢噻喃基、1,1-二氧化四氢噻喃基、四氢呋喃基、二氧杂环己基、吡唑烷基、吡唑啉基、四氢嘧啶基、二氢三唑基、四氢三唑基等;
非芳族稠合杂环基团诸如二氢吲哚基、二氢异吲哚基、二氢苯并呋喃基、二氢苯并二氧杂环己烯基、二氢苯并二氧杂环庚三烯基、四氢苯并呋喃基、色烯基、二氢喹啉基、四氢喹啉基、二氢异喹啉基、四氢异喹啉基、二氢酞嗪基等;等。
本发明的由式(I)表示的芳基烷氧基嘧啶衍生物的盐的例子包括:无机酸盐诸如盐酸盐、硫酸盐、硝酸盐、磷酸盐等、有机酸盐诸如乙酸盐、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;以及与诸如钠离子、钾离子、钙离子、三甲铵等无机或有机碱的盐。
本发明的由式(I)表示的芳基烷氧基嘧啶衍生物及其盐在结构式中可以包含一个或复数个不对称中心,且在某些情况下,可以存在两种或更多种光学异构体和非对映异构体。本发明包括这样的光学异构体中的任一种和以任意比例含有它们的混合物。此外,本发明的由式(I)表示的芳基烷氧基嘧啶衍生物及其盐在结构式中可以具有衍生自碳-碳双键的两类几何异构体。本发明包括所有几何异构体和以任意比例含有它们的混合物。
本发明的式(I)的芳基烷氧基嘧啶衍生物的优选实施方案如下。
R1优选地是
(a1)卤素原子;
(a2)甲酰基;
(a3)氰基;
(a4) (C1-C8)烷基;
(a5) (C3-C8)环烷基;
(a6) (C2-C8)烯基;
(a7) (C2-C8)炔基;
(a8)卤代(C1-C8)烷基;
(a11)卤代(C2-C8)炔基;
(a12) (C1-C8)烷氧基(C1-C8)烷基;
(a13) (C3-C8)环烷基(C1-C8)烷基;
(a14) (C1-C8)烷氧基卤代(C1-C8)烷基;
(a16) (C1-C8)烷硫基(C1-C8)烷基;
(a17) (C1-C8)烷基亚磺酰基(C1-C8)烷基;
(a18) (C1-C8)烷基磺酰基(C1-C8)烷基;
(a27) R4(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a31)芳基;
(a32)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)苯氧基;
(a33)芳基(C1-C8)烷基;
(a37)芳硫基(C1-C8)烷基;
(a39)芳基亚磺酰基(C1-C8)烷基;
(a41)芳基磺酰基(C1-C8)烷基;
(a43) (C1-C8)烷基羰基;
(a45) (C1-C8)烷氧基羰基;
(a46) R4(R5)N羰基,其中R4和R5如上面所定义;
(a47) (C1-C8)烷氧基(C1-C8)烷氧基(C1-C8)烷基;
(a49)杂环基团;
(a50)杂环基团,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)、(t)苯基、(u)氧代基团和(v) (C1-C6)烷氧基羰基(C1-C6)烷基;
(a51)杂环基(C1-C8)烷基;
(a56) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(a57)氧杂环丙基;
(a65)羟基(C1-C8)烷基;
(a66)芳氧基(C1-C8)烷基;
(a67)芳氧基(C1-C8)烷基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基和(s) R4(R5)N羰基,其中R4和R5如上面所定义;
(a81) (杂环基)((C1-C8)烷氧基)(C1-C8)烷基;
(a83)二(C1-C8)烷氧基(C1-C8)烷基,其中所述二(C1-C8)烷氧基的烷氧基可以相同或不同;
(a84)二(C1-C8)烷硫基(C1-C8)烷基,其中所述二(C1-C8)烷硫基的烷基可以相同或不同;
(a85)三(C1-C8)烷基甲硅烷基氧基(C1-C8)烷基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a86)羧基;
(a87)芳氧基羰基;
(a88) C(R4)=NOSO2R5基团,其中R4和R5如上面所定义;
(a89)杂环基亚氨基(C1-C8)烷基;
(a90)三(C1-C8)烷基甲硅烷基(C2-C8)炔基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;
(a91) (C1-C8)烷氧基(C2-C8)炔基;
(a92)羟基(C2-C8)炔基;
(a93) (羟基)((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基;
(a94)二羟基(C1-C8)烷基;
(a95) (羟基)((C1-C8)烷氧基)(C1-C8)烷基;
(a96)二(C1-C8)烷基磺酰氧基(C1-C8)烷基,其中所述二(C1-C8)烷基磺酰氧基的烷基可以相同或不同;
(a97)二((C1-C8)烷氧基(C1-C8)烷氧基)(C1-C8)烷基,其中所述二((C1-C8)烷氧基(C1-C8)烷氧基的烷氧基可以相同或不同;
(a98)二(C1-C8)烷氧基羰基(C2-C8)烯基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a99) (C1-C8)烷氧基羰基(氰基)(C2-C8)烯基;
(a100) ((C1-C8)烷氧基(C1-C8)烷氧基)(羟基)(C1-C8)烷基;
(a101)二氰基(C2-C8)烯基;
(a102) (C3-C8)亚环烷基(C1-C8)烷基;
(a103) (C3-C8)环烷基(羟基)(C1-C8)烷基;
(a104) (C3-C8)环烷基((C1-C8)烷氧基)(C1-C8)烷基;
(a105)杂环基(C2-C8)烯基;
(a106)杂环基(C2-C8)烯基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d)甲酰基、(e) (C1-C6)烷基、(f)卤代(C1-C6)烷基、(g) (C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i) (C3-C6)环烷基(C1-C6)烷氧基、(j) (C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l) (C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n) (C1-C6)烷基磺酰基、(o)卤代(C1-C6)烷基磺酰基、(p) (C1-C6)烷基羰基、(q)羧基、(r) (C1-C6)烷氧基羰基、(s) R4(R5)N羰基(其中R4和R5如上面所定义)和(t)氧代基团;
(a107)卤代(C1-C8)烷基碳酰氧基(C2-C8)烯基;
(a108) (C3-C8)环烷基(卤代(C1-C8)烷基碳酰氧基)(C1-C8)烷基;
(a109) (C1-C8)烷氧基羰基(羟基)(C1-C8)烷基;
(a110)羧基(羟基)(C1-C8)烷基;
(a111)二(C1-C8)烷氧基羰基(C3-C8)环烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a112)二(C1-C8)烷氧基羰基(C1-C8)烷基,其中所述二(C1-C8)烷氧基羰基的烷氧基可以相同或不同;
(a113) (C1-C8)烷基羰基(C2-C8)烯基;
(a114)羟基卤代(C1-C8)烷基;
(a115)二羟基卤代(C1-C8)烷基;
(a116) (C1-C8)烷氧基羰基(C3-C8)环烷基;
(a117)氰基(C3-C8)环烷基;
(a118) (C1-C8)烷氧基羰基(C2-C8)烯基;
(a119)氰基(C2-C8)烯基;
(a120) ((C1-C8)烷氧基)(羟基)卤代(C1-C8)烷基;
(a121) R4(R5)N(C1-C8)烷基(R5)N羰基,其中R4和R5如上面所定义;
(a122) R4(R5)NCO(R5)N(C1-C8)烷基,其中R4和R5如上面所定义;
(a123)三(C1-C8)烷基甲硅烷基(C2-C8)炔基(C2-C8)烯基,其中所述三(C1-C8)烷基甲硅烷基的烷基可以相同或不同;或
(a124)结构式Q7、Q8、Q9、Q10、Q11、Q12、Q13、Q14、Q15、Q16、Q17、Q18、Q19、Q20、Q21、Q22、Q23、Q24、Q25、Q26、Q27、Q28或Q29,其中它们中的每个结构式和符号如上面所定义。
R2和R3可以相同或不同,且每个优选地是
(b1)氢原子;或
(b6)卤代(C1-C8)烷基。
每个X可以相同或不同,且优选地是
(c1)氢原子;
(c2)卤素原子;
(c4)氰基;
(c5)硝基;
(c10) CO(R4)基团,其中R4如上面所定义;
(c14) (C1-C8)烷基;
(c18)卤代(C1-C8)烷基;
(c22)三(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c27) (C1-C8)烷氧基;
(c31)卤代(C1-C8)烷氧基;
(c40)卤代(C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c42) (C1-C8)烷硫基;
(c46)卤代(C1-C8)烷硫基;
(c76)芳基;
(c77)芳基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义;
(c80)芳氧基;或者
(c81)芳氧基,其在环上具有相同或不同的1-5个取代基,所述取代基选自(a)卤素原子、(b)氰基、(c)硝基、(d) (C1-C6)烷基、(e)卤代(C1-C6)烷基、(f) (C1-C6)烷氧基、(g)卤代(C1-C6)烷氧基、(h) (C2-C6)烯基氧基、(i)卤代(C2-C6)烯基氧基、(j) (C2-C6)炔基氧基、(k)卤代(C2-C6)炔基氧基、(l) (C3-C6)环烷基氧基、(m)卤代(C3-C6)环烷基氧基、(n) (C3-C6)环烷基(C1-C6)烷氧基、(o)卤代(C3-C6)环烷基(C1-C6)烷氧基、(p) (C1-C6)烷硫基、(q)卤代(C1-C6)烷硫基、(r) (C1-C6)烷基亚磺酰基、(s)卤代(C1-C6)烷基亚磺酰基、(t) (C1-C6)烷基磺酰基、(u)卤代(C1-C6)烷基磺酰基、(v) N(R4)R5基团(其中R4和R5如上面所定义)、(w) N(R4)COR5基团(其中R4和R5如上面所定义)、(x) N(R4)CO2R5基团(其中R4和R5如上面所定义)、(y) N(R4)SO2R5基团(其中R4和R5如上面所定义)、(z) COR4基团(其中R4如上面所定义)、(aa) CO2R4基团(其中R4如上面所定义)、(bb) CON(R4)R5基团(其中R4和R5如上面所定义)和(cc) C(R4)=NOR5基团,其中R4和R5如上面所定义。
作为Y,CH是优选的。
作为q,1是优选的。
作为m,1或2是优选的。
作为n,0是优选的。
通过例如下述生产方法,可以生产本发明的各种衍生物,且本发明不限于此。
生产方法
其中R1、R2、R3、X、q和m如上面所定义,且Hal是卤素原子。
从式(IV)生产式(II-1)的方法和从式(IV-1)生产式(II-2)的方法
通过在以下文献中公开的方法,可以生产要用作起始原料的式(IV)和式(IV-1)的衍生物:Organic Process Research and Development, 1, 300 (1997), J. Amer.Chem. Soc., 77, 745(1955), WO2001-017975等。
通过使4-羟基嘧啶衍生物(IV)或4,6-二羟基嘧啶衍生物(IV-1)(通过在上述文献中描述的方法生产)与1-10当量的卤化剂在惰性溶剂中反应,可以生产由式(II-1)和(II-2)表示的卤代嘧啶衍生物。卤化剂的例子包括亚硫酰氯、磷酰氯、五氯化磷、三溴化磷(III)等。所述惰性溶剂可以是任意的,只要它不会显著抑制该反应的进程即可,并且可以提及例如:脂族烃诸如己烷、环己烷、甲基环己烷等,卤代烃诸如氯仿、二氯甲烷、四氯化碳等,芳烃诸如苯、二甲苯、甲苯等,链状或环状醚诸如乙醚、叔丁基甲基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷等,腈诸如乙腈、丙腈等,链状或环状酮诸如丙酮、甲基异丁基酮、环己酮等,酯诸如乙酸乙酯、乙酸丁酯等,等。这些惰性溶剂可以单独使用,或可以使用其中2种或更多种的混合物。反应温度可以适当地选自0℃至要使用的惰性溶剂或卤化剂的回流温度。尽管反应时间随反应规模、反应温度等变化且不是恒定的,但是它可以适当地选自几分钟至100小时。尽管所述反应在有空气中的氧等存在下也会进行,但是它可以在惰性气体气氛(诸如氮气、氩气等)中进行。反应结束以后,将目标产物通过常规方法从含有目标产物的反应系统中分离,并在必要时通过重结晶方法、蒸馏方法、柱色谱法方法等进行纯化,以得到目标产物。
从式(II-1)生产式(I-1)的方法和从式(II-2)生产式(II)的方法
在该反应中,在有碱存在下使1-3当量的由式(III)表示的芳基烷基醇衍生物与1当量的由式(II-1)表示的卤代嘧啶衍生物在惰性溶剂中反应,以产生由式(I-1)表示的芳基烷氧基嘧啶衍生物。另外,在有碱存在下使1-1.2当量的由式(III)表示的芳基烷基醇衍生物与1当量的由式(II-2)表示的卤代嘧啶衍生物在惰性溶剂中反应,以产生由式(II)表示的芳基烷氧基嘧啶衍生物。可以用于该反应的惰性溶剂可以是任意的,只要它不会显著抑制反应的进程,且可以提及例如:链状或环状醚诸如乙醚、四氢呋喃、二噁烷等,酮诸如丙酮、甲基乙基酮等,芳烃诸如苯、氯苯等,腈诸如乙腈、丙腈等,酰胺诸如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮等,二甲亚砜,环丁砜等,和水。这些惰性溶剂可以单独使用,或可以使用其中2种或更多种的混合物。可以用于该反应的碱的例子包括:无机碱诸如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸铯、碳酸氢钠、碳酸氢钾等,碱金属氢化物诸如氢化钠、氢化钾等,碱金属烷醇盐诸如甲醇钠、乙醇钠、叔丁氧基钾等,烷基锂诸如甲基锂、正丁基锂等,等。要使用的碱的量通常是由式(III)表示的芳基烷基醇衍生物的约1.0- 1.5摩尔倍。在某些情况下,该反应可以在惰性气体(氮气、氩气)气氛下进行。反应温度可以适当地选自0℃至要用于所述反应的溶剂的沸点。尽管反应时间随反应规模、反应温度等变化且不是恒定的,但是它可以适当地选自几分钟至48小时。反应结束以后,将目标产物通过常规方法从含有目标产物的反应系统中分离,并在必要时通过重结晶方法、蒸馏方法、柱色谱法方法等进行纯化,以得到目标产物。
由式(II)表示的芳基烷氧基嘧啶衍生物是新颖的化合物,其是可用于生产由式(I)表示的芳基烷氧基嘧啶衍生物的合成中间体。作为由Hal表示的卤素原子,氯原子和溴原子是优选的,且氯原子是更优选的。
从式(II)生产式(I-1)的方法
根据在J. Org. Chem., 1955, 20, 225等中描述的方法进行该反应。也就是说,通过在氢气氛下在有碱和催化剂存在下在惰性溶剂中催化氢化由式(II)表示的芳基烷氧基嘧啶衍生物,可以生产由式(I-1)表示的芳基烷氧基嘧啶衍生物。可替换地,通过使用甲酸在反应系统中产生氢来替代氢气氛,可以生产它。
可以用于该反应的催化剂的例子包括四(三苯基膦)钯、钯-碳、铂、雷尼镍等。要使用的催化剂的量是由式(II)表示的芳基烷氧基嘧啶衍生物的约0.0001- 0.1摩尔倍。
该反应在必要时在有相转移催化剂(例如,季铵盐诸如四丁基溴化铵、苄基三乙基溴化铵等,等)存在下进行。
可以用于该反应的碱的例子包括无机碱诸如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸铯、碳酸氢钠、碳酸氢钾等,有机碱诸如三乙胺、吡啶、醋酸钠、乙酸钾等,等。要使用的碱的量通常是由式(II)表示的芳基烷氧基嘧啶衍生物的约0.5-10摩尔倍。
可以用于该反应的惰性溶剂的例子包括:醇诸如甲醇、乙醇等,醚诸如四氢呋喃、二噁烷、二甲氧基乙烷(DME)等,酰胺诸如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮等,水等。这些惰性溶剂可以单独使用,或可以使用其中2种或更多种的混合物。
在该反应中的反应温度通常可以是约0℃至要使用的溶剂的沸点。尽管反应时间随反应规模、反应温度等变化且不是恒定的,但是它可以适当地选自几分钟至48小时。对于在氢气氛下的生产,氢压力可以适当地选自标准压力至10 atm。当使用甲酸时,所述反应优选地在惰性气体气氛(诸如氮气和氩气)下进行。
反应结束以后,可以将目标物质通过常规方法从含有目标物质的反应系统中分离,根据需要,通过使用重结晶方法、蒸馏方法或柱色谱法方法等进行纯化,可以产生目标物质。
从式(I-1)生产式(I)的方法
通过使由式(I-1)表示的芳基烷氧基嘧啶衍生物与氧化剂在惰性溶剂中反应,可以生产由式(I)表示的芳基烷氧基嘧啶衍生物。要用于该反应的氧化剂的例子包括:锰化合物诸如二氧化锰等;铬酸盐诸如铬酸钠等;铅化合物诸如四乙酸铅等;汞化合物诸如氧化汞等;氧化剂诸如四氧化锇、四氧化钌、二氧化硒等;金属卤化物试剂诸如氯化铁、碘化亚铜等;卤素诸如碘、溴等;钯诸如钯/碳等;醌氧化剂诸如DDQ等;过氧化物诸如过氧化氢水溶液、过苯甲酸、间氯过苯甲酸等;等。在这些中,过氧化氢水溶液、过苯甲酸、间氯过苯甲酸是优选的。相对于由式(I-1)表示的芳基烷氧基嘧啶衍生物,这些氧化剂可以适当地选自0.8-10摩尔倍,优选1-2摩尔倍。
在本反应中有用的惰性溶剂可以是任意的,只要它不会显著抑制该反应,且可以提及例如:链状或环状醚诸如乙醚、四氢呋喃、二噁烷等;芳烃诸如苯、甲苯、二甲苯等;卤代烃诸如二氯甲烷、氯仿、四氯化碳等,卤代芳烃诸如氯苯、二氯苯等;腈诸如乙腈等;酯诸如乙酸乙酯等;有机酸诸如甲酸、乙酸等;极性溶剂诸如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。这些惰性溶剂可以单独使用,或使用其中2种或更多种的混合物。
在该反应中的反应温度可以适当地选自-30℃至要使用的惰性溶剂的回流温度。尽管反应时间会随反应规模而变化且不是恒定的,但是它可以适当地选自几分钟至48小时。
反应结束以后,可以将目标物质通过常规方法从含有目标物质的反应系统中分离,根据需要,通过使用重结晶或柱色谱法等进行纯化,可以制造目标物质。
本发明的由式(I)表示的芳基烷氧基嘧啶衍生物的典型例子显示在表1至表12、表14和表15中,本发明不限于此。
在所述表中,“Me”是甲基,“Et”是乙基,“Pr”是丙基,“Bu”是丁基,“Pen”是戊基,“Hex”是己基,“Hep”是庚基,“Oct”是辛基,“Ms”是甲磺酰基,“Bn”是苄基,“Ph”是苯基,“THF”是四氢呋喃基,“THP”是四氢吡喃基,“Py”是吡啶基,“TMS”是三甲基甲硅烷基,“TBDMS”是叔丁基二甲基甲硅烷基,“n-”是正,“i-”是异,“neo-”是新,“s-”是仲,“t-”是叔,“c-”是脂环族烃基,且“=c-Pr”是亚环丙基。显示的性质是熔点(℃)或折射率nD (测量温度;℃)。表13显示了化合物的1H-NMR数据,在表8、9、14和15的性质列中用“NMR”指示。
含有本发明的由式(I)表示的芳基烷氧基嘧啶衍生物或其盐作为活性成分的农业园艺用杀虫剂适合用于防治多种害虫,诸如农业园艺害虫、贮藏谷物害虫、卫生害虫、线虫等,它们对水稻、果树、蔬菜、其它作物、花和观赏植物等有害。
上述有害昆虫、线虫等的例子包括下述。
鳞翅目(Lepidoptera)的害虫的例子包括:褐边缘刺蛾(Parasa consocia)、桥夜蛾(Anomis mesogona)、柑橘凤蝶(Papilio xuthus)、日豆小卷蛾(Matsumuraeses azukivora)、麻田豆秆野螟(Ostrinia scapulalis)、莎草粘虫(Spodoptera exempta)、美国白蛾(Hyphantria cunea)、亚洲玉米螟(Ostrinia furnacalis)、东方粘虫(Pseudaletia separata)、蠹虫(Tinea translucens)、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(Parnara guttata)、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)、苧麻肋野螟蛾(Pleuroptya ruralis)、小蜻蜓尺蛾(Cystidia couaggaria)、亮灰蝶(Lampides boeticus)、透翅天蛾(Cephonodes hylas)、棉铃虫(Helicoverpa armigera)、曼蚕舟蛾(Phalerodonta manleyi)、大避债蛾(Eumeta japonica)、大菜粉蝶(Pieris brassicae)、黄褐天幕毛虫(Malacosoma neustria testacea)、柿举肢蛾(Stathmopoda masinissa)、柿细蛾(Cuphodes diospyrosella)、梣黄卷蛾(Archips xylosteanus)、黄地老虎(Agrotis segetum)、甘蔗黄螟(Tetramoera schistaceana)、黄凤蝶(Papilio machaon hippocrates)、黃斑蝙蝠蛾(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)、葡萄花翅小卷蛾(Lobesia botrana)、中国绿刺蛾(Latoia sinica)、皮暗斑螟(Euzophera batangensis)、慈姑褐纹蛾(Phalonidia mesotypa)、桑斑灯蛾(Spilosoma imparilis)、桑绢野螟(Glyphodes pyloalis)、桑卷叶蛾(Olethreutes mori)、幕谷蛾(Tineola bisselliella)、蝙蝠蛾(Endoclyta excrescens)、谷蛾(Nemapogon granellus)、苹果透翅蛾(Synanthedon hector)、苹果蠹蛾(Cydia pomonella)、小菜蛾(Plutella xylostella)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、蛀茎夜蛾(Sesamia calamistis)、三化螟(Scirpophaga incertulas)、兰草螟蛾(Pediasia teterrellus)、马铃薯块茎蛾(Phthorimaea operculella)、苹蚁舟蛾(Stauropus fagi persimilis)、豆荚螟(Etiella zinckenella)、甜菜夜蛾(Spodoptera exigua)、白斑蝙蝠蛾(Palpifer sexnotata)、灰翅夜蛾(Spodoptera mauritia)、稻白螟(Scirpophaga innotata)、八字地老虎(Xestia c-nigrum)、淡剑纹灰翅夜蛾(Spodoptera depravata)、地中海斑螟(Ephestia kuehniella)、李尺蛾(Angerona prunaria)、分月扇舟蛾(Clostera anastomosis)、大豆夜蛾(Pseudoplusia includens)、松村氏捲蛾(Matsumuraeses falcana)、烟夜蛾(Helicoverpa assulta)、黑点丫纹夜蛾(Autographa nigrisigna)、球菜夜蛾(Agrotis ipsilon)、茶毒蛾(Euproctis pseudoconspersa)、茶小卷叶蛾(Adoxophyes orana)、茶细蛾(Caloptilia theivora)、茶长卷蛾(Homona magnanima)、烟草粉斑螟(Ephestia elutella)、茶避债蛾(Eumeta minuscula)、杨扇舟蛾(Clostera anachoreta)、苜蓿夜蛾(Heliothis maritima)、葡萄长须卷蛾(Sparganothis pilleriana)、玉米茎夜蛾(Busseola fusca)、折带黄毒蛾(Euproctis subflava)、褐纹大尺蛾(Biston robustum)、美洲棉铃虫(Heliothis zea)、甘薯烦夜蛾(Aedia leucomelas)、梨娜刺蛾(Narosoideus flavidorsalis)、梨剑纹夜蛾(Viminia rumicis)、潜蛾(Bucculatrix pyrivorella)、梨小食心虫(Grapholita molesta)、梨潜皮蛾(Spulerina astaurota)、梨云翅斑螟(Ectomyelois pyrivorella)、二化螟(Chilo suppressalis)、葱菜蛾(Acrolepiopsis sapporensis)、印度谷螟(Plodia interpunctella)、菜心野螟蛾(Hellula undalis)、麦蛾(Sitotroga cerealella)、斜纹夜蛾(Spodoptera litura)、绿豆芽蛾(Eucosma aporema)、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(Ostrinia zaguliaevi)、双带夜蛾(Naranga aenescens)、茶蚕(Andraca bipunctata)、葡萄透翅蛾(Paranthrene regalis)、缺角天蛾(Acosmeryx castanea)、葡萄潜叶蛾(Phyllocnistis toparcha)、葡萄浆果蛾(Endopiza viteana)、环针单纹蛾(Eupoecillia ambiguella)、大豆夜蛾(Anticarsia gemmatalis)、烟草云卷蛾(Cnephasia cinereipalpana)、舞毒蛾(Lymantria dispar)、赤松毛虫(Dendrolimus spectabilis)、大豆食心虫(Leguminivora glycinivorella)、豆荚野螟(Maruca testulalis)、豆小卷蛾(Matsumuraeses phaseoli)、大豆丽细蛾(Caloptilia soyella)、柑桔叶潜蛾(Phyllocnistis citrella)、豆啮叶野螟(Omiodes indicate)、杏黄卷蛾(Archips fuscocupreanus)、银纹夜蛾(Acanthoplusia agnata)、Bambalina sp.、桃蛀果蛾(Carposina niponensis)、桃蛀螟(Conogethes punctiferalis)、兴透翅蛾属(Synanthedon sp.)、桃潜蛾(Lyonetia clerkella)、小黄斑粉蝶(Papilio helenus)、斑缘豆粉蝶(Colias erate poliographus)、苹掌舟蛾(Phalera flavescens)、粉蝶科(Pieridae)诸如纹白蝶(Pieris rapae crucivora)、菜粉蝶(Pieris rapae)等、桑毛虫(Euproctis similis)、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)、北川卷蛾(Hoshinoa adumbratana)、圆斑黄枯叶蝶(Odonestis pruni japonensis)、苹剑纹夜蛾(Triaena intermedia)、苹小卷叶蛾(Adoxophyes orana fasciata)、苹小食心虫(Grapholita inopinata)、苹白小卷蛾(Spilonota ocellana)、顶梢卷叶蛾(Spilonota lechriaspis)、梨星毛虫(Illiberis pruni)、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(Pectinophora gossypiella)、棉大卷叶野螟(Notarcha derogata)、瓜绢野螟(Diaphania indica)、烟芽夜蛾(Heliothis virescens)、鼎点钻夜蛾(Earias cupreoviridis)等。
半翅目(Hemiptera)的有害害虫的例子包括:稻绿椿(Nezara antennata)、赤条纤盲蝽(Stenotus rubrovittatus)、黑条红椿象(Graphosoma rubrolineatum)、条赤须盲蝽(Trigonotylus coelestialium)等、黄伊缘蝽(Aeschynteles maculatus)、苍白肉盲蝽(Creontiades pallidifer)
、赤星椿象(Dysdercus cingulatus)、褐圆介壳虫(Chrysomphalus ficus)、枳壳圆蹄盾蚧(Aonidiella aurantii)、油蝉(Graptopsaltria nigrofuscata)、麦长蝽(Blissusleucopterus)、吹绵蚧(Icerya purchasi)、壁椿(Piezodorus hybneri)、稻褐蝽(Lagynotomus elongatus)、白翅叶蝉(Thaia subrufa)、稻黑蝽(Scotinophara lurida)、玫瑰蚜(Sitobion ibarae)、岩崎蝽象(Stariodes iwasakii)、椰圆盾蚧(Aspidiotus destructor)、苍白泰盲蝽(Taylorilygus pallidulus)、杏瘤蚜(Myzusmumecola)、梅白蚧(Pseudaulacaspis prunicola)、豌豆蚜(Acyrthosiphon pisum)、纹须同缘椿象(Anacanthocoris striicornis)、跃盲蝽(Ectometopterus micantulus)、日本二星棒(Eysarcoris lewisi)、巨叶足虫(Molipteryx fuliginosa)、大青叶蝉(Cicadella viridis)、红腹缢管蚜(Rhopalosophum rufiabdominalis)、黑蜡蚧(Saissetia oleate)、温室粉虱(Trialeurodes vaporariorum)、橡木叶蝉(Aguriahana quercus)、草盲蝽属(Lygus spp.)、桦绵斑蚜(Euceraphis punctipennis)、柑橘介壳虫(Andaspis kashicola)、橘软蜡蚧(Coccus pseudomagnoliarum)、甘蔗异背长蝽(Cavelerius saccharivorus)、长贝脊网蝽(Galeatus spinifrons)、菊小长管蚜(Macrosiphoniella sanborni)、黄圆蹄盾蚧(Aonidiella citrina)、茶翅蝽(Halyomorpha mista)、樟网蝽(Stephanitis fasciicarina)、樟个木虱(Trioza camphorae)、中华稻缘蝽(Leptocorisa chinensis)、栎个木虱(Trioza quercicola)、黄角肩网蝽(Uhlerites latius)、葡萄伴斑叶蝉(Erythroneura comes)、长蝽(Paromius exiguus)、柘柳重圆盾蚧(Duplaspidiotus claviger)、二条斑黑尾叶蝉(Nephotettix nigropictus)、庭园盲蝽(Halticiellus insularis)、甘蔗扁角飞虱(Perkinsiella saccharicida)、苹果木虱(Psylla malivorella)、桑木虱(Anomomeura mori)、长尾粉蚧(Pseudococcus longispinis)、桑白盾蚧(Pseudaulacaspis pentagona)、桑绵蜡蚧(Pulvinaria kuwacola)、绿盲蝽(Apolygus lucorum)、葫芦长蝽(Togo hemipterus)、桔二叉蚜(Toxoptera aurantii)、糖粉蚧(Saccharicoccus sacchari)、蔗根蚜(Geoica lucifuga)、瓶额飞虱(Numata muiri)、梨圆介壳虫(Comstockaspis perniciosa)、桔矢尖盾蚧(Unaspis citri)、茄沟无网蚜(Aulacorthum solani)、广二星蝽(Eysarcoris ventralis)、银叶粉虱(Bemisia argentifolii)、大白叶蝉(Cicadella spectra)、春藤圆盾蚧(Aspidiotus hederae)、粟缘蝽(Liorhyssus hyalinus)、黑背丽木虱(Calophya nigridorsalis)、白背稻虱(Sogatella furcifera)、空豆髭长油虫(Megoura crassicauda)、甘蓝蚜(Brevicoryne brassicae)、大豆蚜(Aphis glycines)、稻斑腹蛛缘蝽(Leptocorisa oratorius)、二点黑尾叶蝉(Nephotettix virescens)、莴苣指管蚜(Uroeucon formosanum)、烟盲蝽(Cyrtopeltis tennuis)、烟粉虱(Bemisia tabaci)、桃蜡蚧(Lecanium persicae)、茶糠蚧(Parlatoria theae)、牡丹网纹盾蚧(Pseudaonidia paeoniae)、大贯小绿叶蝉(Empoasca onukii)、褐翅绿椿象(Plautia stali)、百合西圆尾蚜(Dysaphis tulipae)、大戟长管蚜(Macrosiphum euphorbiae)、杜鹃冠网蝽(Stephanitis pyrioides)、角蜡蚧(Ceroplastes ceriferus)、山茶糠蚧(Parlatoria camelliae)、淡娇异蝽(Apolygus spinolai)、黑尾叶蝉(Nephotettix cincticeps)、青蝽(Glaucias subpunctatus)、杂毛合垫盲蝽(Orthotylus flavosparsus)、玉米蚜(Rhopalosiphum maidis)、玉米蜡蝉(Peregrinus maidis)、二星蝽(Eysarcoris parvus)、温带臭虫(Cimex lectularius)、冷杉木虱(Psylla abieti)、褐飞虱(Nilaparvata lugens)、海桐木虱(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(Stephanitis nashi)、水松粉蚧(Dysmicoccus wistariae)、梨蚧(Lepholeucaspis japonica)、梨园尾蚜(Sappaphis piri)、萝卜蚜(Lipaphis erysimi)、台湾韭蚜(Neotoxoptera formosana)、莲缢管蚜(Rhopalosophum nymphaeae)、蔷薇小叶蝉(Edwardsianarosae)、苏铁褐点盾蚧(Pinnaspisaspidistrae)、赤杨木虱(Psylla alni)、叶蝉(Speusotettix subfusculus)、杂食性叶蝉(Alnetoidia alneti)、稗飞虱(Sogatella panicicola)、苜蓿盲蝽(Adelphocoris lineolatus)、联斑棉红蝽(Dysdercus poecilus)、黑片盾蚧(Parlatoria ziziphi)、褐角肩网蝽(Uhlerites debile)、灰飞虱(Laodelphax striatellus)、六斑菜蝽(Eurydema pulchrum)、长肩棘缘椿象(Cletus trigonus)、一点铲头沫蝉(Clovia punctata)、小绿叶蝉(Empoasca sp.)、褐软蜡蚧(Coccus hesperidum)、草鼓胸长蝽(Pachybrachius luridus)、藤臀纹粉蚧(Planococcus kraunhiae)、双斑盲蝽(Stenotus binotatus)、葡萄阿小叶蝉(Arboridia apicalis)、二点叶蝉(Macrosteles fascifrons)、斑须蝽(Dolycoris baccarum)、三环苜蓿盲蝽(Adelphocoris triannulatus)、葡萄根瘤蚜(Viteus vitifolii)、瘤缘椿象(Acanthocoris sordidus)、大稻缘蝽(Leptocorisa acuta)、瘤腹巨股长蝽(Macropes obnubilus)、稻棘缘蝽(Cletus punctiger)、点蜂缘椿象(Riptortus clavatus)、番茄木虱(Paratrioza cockerelli)、柳尖胸沫蝉(Aphrophora costalis)、日本草盲蝽(Lygus disponsi)、东亚草盲蝽(Lygus saundersi)、松白粉蚧(Crisicoccus pini)、松小叶蝉(Empoasca abietis)、松粉蚧(Crisicoccus matsumotoi)、豆蚜(Aphis craccivora)、臭蝽(Megacopta punctatissimum)、圆白星椿象(Eysarcoris guttiger)、紫疤蛎盾蚧(Lepidosaphes beckii)、柑桔木虱(Diaphorina citri)、桔蚜(Toxoptera citricidus)、柑桔粉蚧(Planococcus citri)、柑桔粉虱(Dialeurodes citri)、黑刺粉虱(Aleurocanthus spiniferus)、桔小粉蚧(Pseudococcus citriculus)、小桔塔叶蝉(Zyginella citri)、桔绵蜡蚧(Pulvinaria citricola)、偏软蜡蚧(Coccus discrepans)、蛇眼臀网盾蚧(Pseudaonidia duplex)、柑橘绵蚧(Pulvinaria aurantii)、东方球蜡蚧(Lecanium corni)、稻绿蝽(Nezara viridula)、二刺狭盲蝽(Stenodema calcaratum)、禾谷缢管蚜(Rhopalosiphum padi)、麦长管蚜(Sitobion akebiae)、麦二叉蚜(Schizaphis graminum)、麦叶蝉(Sorhoanus tritici)、光管舌尾蚜(Brachycaudus helichrysi)、紫翅果蝽(Carpocoris purpureipennis)、桃蚜(Myzus persicae)、桃大尾蚜(Hyalopterus pruni)、柳蚜(Aphis farinose yanagicola)、杨柳网蝽(Metasalis populi)、矢尖盾蚧(Unaspis yanonensis)、芙蓉木虱(Mesohomotoma camphorae)、绣线菊蚜(Aphis spiraecola)、苹果蚜(Aphis pomi)、榆蛎盾蚧(Lepidosaphes ulmi)、苹木虱(Psylla mali)、苹叶盲蝽(Heterocordylus flavipes)、苹果瘤蚜(Myzus malisuctus)、苹果蚜虫(Aphidonuguis mali)、苹果叶蝉(Orientus ishidai)、苹果蚜(Ovatus malicolens)、苹绵蚜(Eriosoma lanigerum)、红蜡蚧(Ceroplastes rubens)、棉蚜(Aphis gossypii)等。
鞘翅目(Coleoptera)的害虫的例子包括:合欢双条天牛(Xystrocera globosa)、毒隐翅虫(Paederus fuscipes)、金边青花金龟(Eucetonia roelofsi)、绿豆象(Callosobruchus chinensis)、甘薯小象(Cylas formicarius)、紫苜蓿叶象(Hypera postica)、稻象甲(Echinocnemus squameus)、水稻负泥虫(Oulema oryzae)、长腿水叶甲(Donacia provosti)、稻水象甲(Lissorhoptrus oryzophilus)、甘薯叶甲(Colasposoma dauricum)、西印度甘薯象甲(Euscepes postfasciatus)、墨西哥豆瓢虫(Epilachna varivestis)、菜豆象(Acanthoscelides obtectus)、玉米根叶甲(Diabrotica virgifera virgifera)、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)、黄星天牛(Psacothea hilaris)、黄斑天牛(Aeolesthes chrysothrix)、蒙栎象(Curculio sikkimensis)、酱曲露尾甲(Carpophilus hemipterus)、小青花金龟(Oxycetonia jucunda)、根萤叶甲属(Diabrotica spp.)、亮绿彩丽金龟(Mimela splendens)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium castaneum)、米象(Sitophilus oryzae)、亚扁粉盗(Palorus subdepressus)、日本豆金龟(Melolontha japonica)、星天牛(Anoplophora malasiaca)、大点拟粉虫(Neatus picipes)、马铃薯叶甲(Leptinotarsa decemlineata)、黄瓜十一星叶甲食根亚种(Diabrotica undecimpunctata howardi)、猎象(sphenophorus venatus)、十四点负泥虫(Crioceris quatuordecimpunctata)、梅球颈象(Conotrachelus nenuphar)、大根猿象虫(Ceuthorhynchidius albosuturalis)、小猿叶虫(Phaedon brassicae)、烟草甲(Lasioderma serricorne)、日本根瘤象(Sitona japonicus)、斑喙丽金龟(Adoretus tenuimaculatus)、面粉甲虫(Tenebrio molitor)、黄粉虫猴子甲虫(Basilepta balyi)、小车轴草叶象甲(Hypera nigrirostris)、甜菜跳甲(Chaetocnema concinna)、绿丽金龟(Anomala cuprea)、黑七鳃金龟(Heptophylla picea)、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 unicolor japonicus)、斑鞘豆叶甲(Pagria signata)、红铜丽金龟(Anomala rufocuprea)、姬帕谷甲(Palorus ratzeburgii)、褐菌虫(Alphitobius laevigatus)、地毯甲虫(Anthrenus verbasci)、褐粉蠹(Lyctus brunneus)、杂拟谷盗(Tribolium confusum)、黑条麦萤叶甲(Medythia nigrobilineata)、葡萄脊虎天牛(Xylotrechus pyrrhoderus)、黄瓜跳甲(Epitrix cucumeris)、纵坑切梢小蠹(Tomicus piniperda)、松墨天牛(Monochamus alternatus)、日本豆金龟(Popillia japonica)、豆芫青(Epicauta gorhami)、玉米象(Sitophilus zeamais)、日本苹虎象(Rhynchites heros)、蔬菜叶象甲(Listroderes costirostris)、四纹豆象(Callosobruchus maculatus)、苹霜绿切叶象(Phyllobius armatus)、苹果开花象鼻虫(Anthonomus pomorum)、铜绿里叶甲(Linaeidea aenea)、墨西哥棉铃象(Anthonomus grandis)等。
双翅目(Diptera)的害虫的例子包括:淡色库蚊(Culex pipiens pallens)、甜菜潜叶蝇(Pegomya hyoscyami)、南美斑潜蝇(Liriomyza huidobrensis)、家蝇(Musca domestica)、稻秆蝇(Chlorops oryzae)、稻心蝇(Hydrellia sasakii)、日本稻潜蝇(Agromyza oryzae)、姬稻潜叶蝇(Hydrellia griseola)、菜豆蛇潜蝇(Ophiomyia phaseoli)、瓜实蝇(Dacuscucurbitae)、樱桃果蝇(Drosophila suzukii)、日本樱桃实蝇(Rhacochlaena japonica)、厩腐蝇(Muscina stabulans)、蚤蝇科(Phoridae)诸如东亚异蚤蝇(Megaselia spiracularis)等、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)、甘蓝地种蝇(Hylemya brassicae)、瘿蚊属(Asphondylia sp.)、灰地种蝇(Delia platura)、葱地种蝇(Delia antiqua)、樱桃绕实绳(Rhagoletis cerasi)、地下家蚊(Culex pipiens molestus Forskal)、地中海实蝇(Ceratitis capitata)、黑翅蕈蝇(Bradysia agrestis)、肖藜泉蝇(Pegomya cunicularia)、美洲斑潜蝇(Liriomyza sativae)、番茄斑潜蝇(Liriomyza bryoniae)、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(Aedes albopictus)、三叶斑潜蝇(Liriomyza trifolii)、美洲斑潜蝇(Liriomyza sativae)、东方果实蝇(Dacus dorsalis)、蜜柑大实蝇(Dacus tsuneonis)、麦红吸浆虫(Sitodiplosis mosellana)、黑腹麦秆蝇(Meromuza nigriventris)、墨西哥按实蝇(Anastrepha ludens)、苹果实蝇(Rhagoletis pomonella)等。
膜翅目(Hymenoptera)的害虫的例子包括:短刺棱胸切叶蚁(Pristomyrmex pungens)、肿腿蜂科(Bethylidae)、法老蚁(Monomorium pharaohnis)、宽节大头蚁(Pheidole noda)、菜叶蜂(Athalia rosae)、栗瘿蜂(Dryocosmus kuriphilus)、日本黑褐蚁(Formica fusca japonica)、胡蜂总科(Vespoidea)、黑背白萝卜叶蜂(Athalia infumata)、月季叶蜂(Arge pagana)、日本芜菁叶蜂(Athalia japonica)、切叶蚁属(Acromyrmex spp.)、火蚁属(Solenopsis spp.)、苹果三节叶蜂(Arge mali)、光滑管琉璃蚁(Ochetellus glaber)等。
直翅目(Orthoptera)的害虫的例子包括:南方稻草螽(Homorocoryphus lineosus)、蝼蛄属(Gryllotalpa sp.)、小稻蝗(Oxya hyla intricata)、小翅稻蝗(Oxya yezoensis)、飞蝗(Locusta migratoria)、日本稻蝗(Oxya japonica)、北方水稻螽斯(Homorocoryphus jezoensis)、黄脸油葫芦(Teleogryllus emma)等。
蓟马科(Thripidae)的害虫的例子包括:红带滑胸针蓟马(Selenothrips rubrocinctus)、稻蓟马(Stenchaetothrips biformis)、稻管蓟马(Haplothrips aculeatus)、柿管蓟马(Ponticulothrips diospyrosi)等、黄蓟马(Thrips flavus)、玉米黄呆蓟马(Anaphothrips obscurus)、佛州樟蓟马(Liothrips floridensis)、唐菖蒲简蓟马(Thrips simplex)、菊黑毛蓟马(Thrips nigropilosus)、温室蓟马(Heliothrips haemorrhoidalis)、桑蓟马(Pseudodendrothrips mori)、腹小头蓟马(Microcephalothrips abdominalis)、帕氏毛管蓟马(Leeuwenia pasanii)、Litotetothrips pasaniae、柑桔硬蓟马(Scirtothrips citri)、华简管蓟马(Haplothrips chinensis)、豆喙蓟马(Mycterothrips glycines)、毛蓟马(Thrips setosus)、茶黄蓟马(Scirtothrips dorsalis)、茶棍蓟马(Dendrothrips minowai)、黑角简管蓟马(Haplothrips niger)、烟蓟马(Thrips tabaci)、葱蓟马(Thrips alliorum)、黄胸蓟马(Thrips hawaiiensis)、豆简管蓟马(Haplothrips kurdjumovi)、袖指蓟马(Chirothrips manicatus)、花蓟马(Fankliniella intonsa)、日本蓟马(Thrips coloratus)、西花蓟马(Franklinella occidentalis)、棕榈蓟马(Thrips palmi)、百合蓟马(Frankliniella lilivora)、百合滑管蓟马(Liothrips vaneeckei)等。
蜱螨亚纲(Acari)的害虫的例子包括:红纤沙螨(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(Demodex canis)、山楂叶螨(Tetranychus viennensis)、神泽氏叶螨(Tetranychus kanzawai)、硬蜱属(Ixodes)诸如血红扇头蜱(Rhipicephalus sanguineus)等、马六甲肉食螨(Cheyletus malaccensis)、腐食酪螨(Tyrophagus putrescentiae)、粉剂螨(Dermatophagoides farinae)、红背蜘蛛(Latrodectus hasseltii)、台湾革蜱(Dermacentor taiwanicus)、茶尖叶节蜱(Acaphylla theavagrans)、侧多食跗线螨(Polyphagotarsonemus latus)、番茄刺皮瘿螨(Aculops lycopersici)、林禽刺螨(Ornithonyssus sylvairum)、二斑叶螨(Tetranychus urticae)、中国瘿螨(Eriophyes chibaensis)、人疥螨(Sarcoptes scabiei)、长角血蜱(Haemaphysalis longicornis)、有胛硬蜱(Ixodes scapularis)、似食酪螨(Tyrophagus similis)、普通肉食螨(Cheyletus eruditus)、柑桔全爪螨(Panonychus citri)、莫氏肉食螨(Cheyletus moorei)、紫红短须螨(Brevipalpus phoenicis)、犬猫耳螨(Octodectes cynotis)、欧洲室尘螨(Dermatophagoides ptrenyssnus)、褐黄血蜱(Haemaphysalis flava)、卵形硬蜱(Ixodes ovatus)、琉球柑橘锈螨(Phyllocoptruta citri)、苹刺瘿螨(Aculus schlechtendali)、苹果全爪螨(Panonychus ulmi)、美洲花蜱(Amblyomma americanum)、鸡皮刺螨(Dermanyssus gallinae)、罗宾根螨(Rhyzoglyphus robini)、Sancassania sp.等。
Termitidaenoxious的害虫的例子包括:奄美大白蚁(Reticulitermes miyatakei)、小楹白蚁(Incisitermes minor)、家白蚁(Coptotermes formosanus)、日本湿木蚁(Hodotermopsis japonica)、散白蚁属(Reticulitermes spp.)、黄胸散白蚁(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)、中岛白蚁(Glyptotermes nakajimai)、近扭白蚁(Pericapritermes nitobei)、黄胸散白蚁(Reticulitermess peratus)等。
蜚蠊目(Blattaria)的害虫的例子包括:烟色大蠊(Periplaneta fuliginosa)、德国小蠊(Blattella germanica)、东方蜚蠊(Blatta orientalis)、褐色大蠊(Periplaneta brunnea)、拟德国小蠊(Blattella lituricollis)、日本大蠊(Periplaneta japonica)、美洲大蠊(Periplaneta Americana)等。
蚤目(Aphaniptera)的例子包括:人蚤(Pulex irritans)、猫栉首蚤(Ctenocephalides felis)和鸡角叶蚤(Ceratophyllus gallinae)等。
线虫门(Nematoda)的例子包括:草莓芽线虫(Nothotylenchus acris)、稻叶牙滑刃线虫(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)、半穿剌线虫(Tylenchus semipenetrans)等。
Malacozoa的例子包括:福寿螺(Pomacea canaliculata)、非洲大蜗牛(Achatina fulica)、双线蛞蝓(Meghimatium bilineatum)、瓦伦西亚列蛞蝓(Lehmannina valentiana)、黄蛞蝓(Limax flavus)、螺蛳(Acusta despecta sieboldiana)等。
本发明的农业园艺用杀虫剂还对作为其它害虫的番茄潜叶虫(番茄斑潜蝇(Tuta absoluta))具有强防治作用。
另外,作为动物寄生的螨属(Acari)(其为防治靶标之一),可以提及例如:硬蜱属(Ixodes)诸如微小牛蜱(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)、大刺血蜱(Haemaphysalis megaspinosa)、网纹革蜱(Dermacentor reticulatus)和台湾革蜱(Dermacentor taiwanesis),禽刺螨属(Ornithonyssus)诸如鸡皮剌螨(Dermanyssus gallinae)、北方刺脂螨(Ornithonyssus sylviarum)和囊形刺脂螨(Ornithonyssus bursa),恙螨属(Trombicula)诸如威氏真恙螨(Eutrombicula wichmanni)、红纤恙螨(Leptotrombidium akamushi)、苍白纤恙螨(Leptotrombidium pallidum)、富士纤恙螨(Leptotrombidium fuji)、Leptotrombidium tosa、秋收新恙螨(Neotrombicula autumnalis)、阿氏真恙螨(Eutrombicula alfreddugesi)和宫川合轮恙螨(Helenicula miyagawai),肉食螨科(Cheyletidae)诸如雅氏姬螯螨(Cheyletiella yasguri)、兔皮姬螯螨(Cheyletiella parasitivorax)和布氏姬螯螨(Cheyletiella blakei),疥螨属(Sarcoptes)诸如免痒螨(Psoroptes cuniculi)、牛痒螨(Chorioptes bovis)、狗耳疥螨(Otodectes cynotis)、人疥螨(Sarcoptes scabiei)和猫耳螨(Notoedres cati),蠕形螨科(Demodicidae)诸如犬蠕形螨(Demodex canis)等。
作为蚤(其为另一种防治靶标),可以提及例如:属于蚤目(Siphonaptera)的外寄生性无翅昆虫,更具体地为属于蚤科(Pulicidae)和欧洲鼠蚤科(Ceratephyllus)等的蚤。属于蚤科(Pulicidae)的蚤的例子包括:犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、禽角头蚤(Echidnophaga gallinacea)、印鼠客蚤(Xenopsylla cheopis)、缓慢细蚤(Leptopsylla segnis)、条纹鼠蚤(Nosopsyllus fasciatus)、不等单蚤(Monopsyllus anisus)等。
外部寄生虫(其为另一种防治靶标)的例子包括:虱目(Anoplura)诸如短吻牛虱(阔胸血虱(Haematopinus eurysternus))、马吸吮虱(驴血虱(Haematopinus asini))、绵羊虱(羊虱(Dalmalinia ovis))、长吻牛虱(牛颚虱(Linognathus vituli))、猪虱(猪血虱(Haematopinus suis))、阴虱(阴虱(Phthirus pubis))和头虱(头虱(Pediculus humanus capitis));啮毛虱诸如狗啮毛虱(狗嚼虱(Trichodectes canis));和吸血的双翅昆虫诸如虻(三角虻(Tabanus trigonus))、咬蠓(虚库蠓(Culicoides schultzei))和蚋(饰蚋(Simulium ornatum))。此外,内部寄生虫的例子包括:线虫类诸如肺虫、鞭虫、结节状线虫、胃寄生虫、蛔虫和丝虫;多节绦虫诸如猬叠宫绦虫(Spirometra erinacei)、阔节裂头绦虫(Diphyllobothrium latum)、犬复殖孔绦虫(Dipylidium caninum)、多头绦虫(Taenia multiceps)、细粒棘球绦虫(Echinococcus granulosus)和多房棘球绦虫(Echinococcus multilocularis);吸虫类诸如日本血吸虫(Schistosoma japonicum)和肝片形吸虫(Fasciola hepatica);和原生动物类诸如球虫、疟原虫、肠肉孢子虫、弓形虫和隐孢子虫。
含有本发明的由式(I)表示的芳基烷氧基嘧啶衍生物或其盐作为活性成分的农业园艺用杀虫剂对于以上举例的害虫具有显著防治作用,所述害虫对水田作物、旱地作物、果树、蔬菜和其它作物、花卉和观赏植物等有害。因此,通过在预计害虫会出现的时期、在它们出现之前或在已证实它们出现时,将所述药剂施用到培育载体诸如繁殖设施、水田、田地、果树、蔬菜、其它作物或花卉和观赏植物等的种子、水田水、茎和叶子、或土壤,可以表现出本发明的农业园艺用杀虫剂的期望效果。具体地,优选的使用形式是如下利用被称作渗透转移性的施用:对作物、花卉和观赏植物等的育苗土壤、移植时的植穴土壤、作物根部、灌溉水、水耕栽培中的栽培水等进行处理,经由土壤或不经由土壤而从根部吸收本发明的化合物。
可采用本发明的农业园艺用杀虫剂的经济植物没有特别限定,可以提及例如:植物诸如谷类(例如水稻、大麦、小麦、黑麦、燕麦、玉米等);豆类(大豆、赤豆、蚕豆、豌豆、菜豆、花生等);果树和水果(苹果、柑橘类、梨、葡萄、桃、李子、樱桃、胡桃、栗子、扁桃、香蕉等);蔬菜(甘蓝、番茄、菠菜、花茎甘蓝、莴苣、洋葱、大葱(细香葱、大葱)、青椒、茄子、草莓、胡椒、秋葵、韭葱等),根菜类(胡萝卜、马铃薯、甘薯、芋头、萝卜、芜菁、莲藕、牛蒡、大蒜、日本韭葱等),加工用作物(棉花、大麻、甜菜、啤酒花、甘蔗、甜菜、橄榄、橡胶、咖啡、烟草、茶等);瓜类(南瓜、黄瓜、西瓜、香瓜、甜瓜等);饲料作物(野茅、高粱、梯牧草、三叶草、苜蓿等);草坪植物(高丽芝草、糠穗草等);香料作物(薰衣草、迷迭香、百里香、香菜、胡椒、姜等);花卉(菊花、蔷薇、香石竹、兰科植物、郁金香、百合等)、庭院树木(银杏、日本山樱、桃叶珊瑚等)、林木(库页冷杉(Abies sachalinensis)、鱼鳞云杉(Picea jezoensis)、松木、罗汉柏(Thujopsis dolabrata)、日本香柏(Japanese cedar)、日本扁柏(Japanese cypress)、桉树等)等。
上述“植物”还包括通过经典培育方法或基因重组技术而对除草剂具有抗性的植物,所述除草剂是例如:HPPD抑制剂诸如异噁唑草酮等,ALS抑制剂诸如咪草烟、噻吩磺隆等,EPSP合酶抑制剂诸如草甘膦等,谷氨酰胺合酶抑制剂诸如草铵膦等,乙酰基辅酶A羧化酶抑制剂诸如烯禾啶等,溴苯腈(Broxynil),麦草畏,2,4-滴等。
通过经典培育方法而被赋予抗性的“植物”的例子包括:对咪唑啉酮ALS抑制性的除草剂诸如咪草烟等具有抗性的油菜、小麦、向日葵和稻,其已经作为Clearfield(注册商标)的商业名称商购可得。类似地,通过经典培育方法而对磺酰脲ALS抑制性的除草剂诸如噻吩磺隆等具有抗性的大豆已经作为STS大豆的商业名称商购可得。类似地,通过经典培育方法而对乙酰基辅酶A羧化酶抑制剂诸如三酮肟和芳氧基苯氧基丙酸除草剂等具有抗性的植物的例子包括有SR玉米等。
对乙酰基辅酶A羧化酶抑制剂具有抗性的植物记载于Proc. Natl. Acad. Sci.USA, 第87卷, 第7175页- 7179 (1990)等。另外,在Weed Science, 第53卷, 第728页-746 (2005)等中报道了对乙酰基辅酶A羧化酶抑制剂具有抗性的突变乙酰基辅酶A羧化酶,并且可以如下建立对乙酰基辅酶A羧化酶抑制剂具有抗性的植物:通过基因重组技术将这样的突变乙酰基辅酶A羧化酶基因引入到植物中,或者将参与提供抗性的突变引入植物的乙酰基辅酶A羧化酶中。此外,可以如下建立对乙酰基辅酶A羧化酶抑制剂、ALS抑制剂等具有抗性的植物:通过以嵌合修复技术(Gura T. 1999. Repairing the Genome’s SpellingMistakes. Science 285: 316-318.)为代表的、将碱基置换突变核酸引入到植物细胞内,从而将位点特异性的氨基酸置换突变引入到植物的乙酰基辅酶A羧化酶、ALS基因等中。本发明的农业园艺用杀虫剂也可以用于这些植物。
此外,在这样的遗传修饰的植物中产生的毒素的例子包括:从蜡状芽孢杆菌(Bacillus cereus)或日本甲虫芽孢杆菌(Bacillus popilliae)衍生出的杀虫蛋白;从苏云金芽孢杆菌(Bacillus thuringiensis)衍生出的杀虫蛋白诸如δ-内毒素(例如CrylAb、CrylAc、CrylF、CrylFa2、Cry2Ab、Cry3A、Cry3Bbl和Cry9C)、VIP1、VIP2、VIP3和VIP3A;从线虫衍生出的毒素;由动物产生的毒素,诸如蝎毒素、蜘蛛毒素、蜜蜂毒素和昆虫-特异性的神经毒素;丝状真菌毒素;植物凝集素;凝集素;蛋白酶抑制剂诸如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯块茎特异蛋白(patatin)、半胱氨酸蛋白酶抑制剂和木瓜蛋白酶抑制剂;核糖体灭活蛋白(RIP)诸如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、rufin、sapolin和priodin;类固醇代谢酶诸如3-羟基类固醇氧化酶、脱皮甾醇-UDP-葡萄糖基转移酶和胆固醇氧化酶;蜕皮激素抑制剂;HMG-CoA还原酶;离子通道抑制剂诸如钠通道抑制剂和钙通道抑制剂;保幼激素酯酶;利尿剂激素受体;均二苯乙烯合成酶;联苄合成酶;壳多糖酶;葡聚糖酶等。
在这样的遗传修饰的植物中产生的毒素还包括:杀虫蛋白的杂合毒素、部分缺失的毒素和经修饰的毒素,诸如δ-内毒素蛋白(例如CrylAb、CrylAc、CrylF、CrylFa2、Cry2Ab、Cry3A、Cry3Bbl、Cry9C、Cry34Ab和Cry35Ab)、VIPl、VIP2、VIP3和VIP3A。通过采用重组技术将这样的蛋白的不同结构域进行新颖的组合,生产杂合毒素。已知的部分缺失的毒素是CrylAb,其中缺失了氨基酸序列的一部分。在经修饰的毒素中,天然毒素的一个或多个氨基酸被置换。
这样的毒素的例子以及能够合成这样的毒素的遗传修饰的植物描述在EP-A-0374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878、WO 03/052073等中。
这样的遗传修饰的植物中包含的毒素会给植物赋予对鞘翅目害虫、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也可以与这些技术联用或者体系化使用。
为了防治各种害虫,只需要将本发明的农业园艺用杀虫剂直接、或用水等适当稀释或混悬于其中后,以对防治害虫或线虫有效的量施用于预计会出现害虫和线虫的植物。例如,对于果树、谷类、蔬菜等中出现的害虫和线虫,将杀虫剂喷洒在茎部和叶部,或者通过以下处理而从根部吸收,所述处理是:种子处理,诸如将种子浸入药剂中、拌种(dressingof seeds)、Calper处理等;土壤处理,诸如土壤全层掺合、播种沟施用、床土掺合、窝眼(cell seedling)处理、栽植穴处理、植物根处理、施顶肥、水稻的箱处理(box treatment)、水面施用等,等。此外,农业园艺用杀虫剂还可以通过施用于培养液(水耕)栽培的培养液中、利用烟熏或树干注射等的施用来使用。
只需要将本发明的农业园艺用杀虫剂直接、或用水等适当稀释或混悬于其中后,以对防治害虫有效的量施用于预计会产生害虫的地方。例如还可如下应用:喷洒于谷物贮存害虫、住宅害虫、卫生害虫、森林害虫等,以及对住宅和建材等涂布、烟熏、施毒饵等。
作为种子处理的方法,可以提及常规的方法,例如:包含将种子浸渍于通过稀释或未稀释液体制剂或固体制剂所得的液体药剂中而使药剂浸透的方法、包含通过使种子与制剂混合或进行拌药(dressing)等而将固体制剂或液体制剂黏附于种子表面的方法、包含用粘性载体(例如,树脂、聚合物等)与制剂混合并在种子上形成涂层的方法、以及包含种植时同时施用在种子附近的方法等。
上述待进行种子处理的“种子”是指用于繁殖的处于栽培初期的植物体,并且包括种子、以及球茎、块茎、种块、胚芽、繁殖体、鳞茎、利用插枝繁殖的营养繁殖用植物体等。
在实施本发明的使用方法时,植物的“土壤”和“培育载体”是指栽培植物用的支撑体,尤其是用于根生长的支撑体,并且材质不受特别限制。只要植物能在其中生长则任何材质皆可,具体的材质包括例如土壤、育苗床、水等。作为具体的材质还可使用砂、浮石、蛭石、硅藻土、琼脂、凝胶状物质、聚合物物质、岩绵、玻璃绵、木片、树皮等。
作为向作物的茎和叶、或者储藏谷物害虫、住宅害虫、卫生害虫、森林害虫等施用的方法,可以提及如下方法:包括用水适当稀释液体制剂(诸如乳剂、可流动制剂等)或固体制剂(诸如可湿性粉剂或水分散颗粒剂等),并将其喷洒的方法;喷洒粉剂的方法;或者烟熏等。
至于施用至土壤,例如可以提及如下方法:包括将在水中稀释或未稀释的液体制剂施用于植物体的植物养料、育苗用苗圃等的方法;包括将颗粒剂施用于植物体的植物养料或育苗用苗圃等的方法;包括在播种前或移植前施用粉剂、可湿性粉剂、水分散颗粒剂、颗粒剂等而允许它们混入土壤整体的方法;包括在播种前或种植前向种植穴、播种沟等施用可湿性粉剂、水分散颗粒剂、颗粒剂等的方法等。
在水稻的育苗箱的情况中,剂型可根据时机,例如播种时施用、绿化时施用、移植时施用等而改变。可以应用粉剂、水分散颗粒剂、颗粒剂等剂型。还可通过混入培养土(grove soil)中而进行施用,其中该培养土可与粉剂、水分散颗粒剂、颗粒剂等混合,例如,可采用混入床土、混入覆土、混入培养土整体等。简单地,培养土与各种制剂可以以交互层形式施用。
作为施用至水田的方法,通常将大型喷洒剂(jumbo)、装填剂(pack)、颗粒剂、水分散颗粒剂等固体制剂;流动剂、乳剂等液体制剂喷洒于淹水田。可替代地,还可以在插秧时将合适的制剂直接或与肥料混合后施用于或注入土壤中。另外,通过将乳剂、流动剂等液体剂应用于进水口和诸如灌溉设备等流向水田的水流源头,也可以在供水的过程中省力地施用。
对旱地作物,可以在播种至育苗期期间,对种子、欲放置在植物体附近的培育载体等进行处理。对欲直接播种于田地的植物,优选的是对种子的直接处理、栽培时对植物的植物养料的处理等。可以进行颗粒剂的施用、使用以水稀释或未稀释的液体剂的土壤注入处理等。在播种前将颗粒剂与培育载体掺合并播种该掺合物也是优选的处理。
对欲移植的栽培植物在播种或育苗期的处理,优选的是种子的直接处理、以液体剂进行育苗用苗圃的土壤灌注处理、或以颗粒剂进行其分散处理。此外,定植时以颗粒剂处理种植穴、将欲放置于移植处附近的培育载体与颗粒剂混合也是优选的处理。
本发明的农业园艺用杀虫剂通常根据农用化学品的一般配制方式制备成方便可用的形式。
也就是说,将本发明的由式(I)表示的芳基烷氧基嘧啶氧化物衍生物或其盐与合适的惰性载体和任选的佐剂以适当比例掺合并通过溶解、分散、悬浮、混合、浸渍、吸附或粘着而制备成合适的制剂形式,如悬浮液、可乳化浓缩物、可溶性浓缩物、可湿性粉剂、水分散颗粒剂、颗粒剂、粉剂、片剂、装填剂等。
除活性成分以外,本发明的组合物(农业园艺用杀虫剂或动物寄生虫防治剂)还可以根据需要含有通常用于杀虫剂制剂或动物寄生虫防治剂的额外组分。所述额外组分的例子包括:载体(诸如固体载体、液体载体等)、表面活性剂、分散剂、润湿剂、粘合剂、增粘剂、增稠剂、着色剂、展着剂、粘着剂、防冻剂、防结块剂、崩解剂、稳定剂等。在必要时,还可以使用防腐剂、植物碎屑等作为其它额外组分。这些额外组分可以单独使用,或使用其中2种或更多种的混合物。
固体载体的例子包括:天然矿物诸如石英、粘土、高岭石、叶蜡石、绢云母、滑石粉、膨润土、酸性粘土、绿坡缕石、沸石、硅藻土等;无机盐诸如碳酸钙、硫酸铵、硫酸钠、氯化钾等;有机固体载体诸如合成的硅酸、合成的硅酸盐、淀粉、纤维素、植物粉末(例如,锯屑、椰壳、玉米穗轴、烟草秆等)等;塑料载体诸如聚乙烯、聚丙烯、聚偏二氯乙烯等;脲,中空无机体、中空体塑料、烟雾硅胶(白炭墨)等。这些可以单独使用,或使用其中2种或更多种的混合物。
液体载体的例子包括:醇,包括一元醇(诸如甲醇、乙醇、丙醇、异丙醇、丁醇等)和多元醇(诸如乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、甘油等);多元醇化合物诸如丙二醇醚等;酮诸如丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮等;醚诸如乙醚、二噁烷、乙二醇单乙基醚、二丙基醚、四氢呋喃等;脂族烃诸如正石蜡、环烷烃、异石蜡、煤油、矿物油等;芳烃诸如苯、甲苯、二甲苯、溶剂石脑油、烷基萘等;卤代烃诸如二氯甲烷、氯仿、四氯化碳等;酯诸如乙酸乙酯、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;内酯诸如γ-丁内酯等;酰胺诸如二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺、N-烷基吡咯烷酮等;腈诸如乙腈等;硫化合物诸如二甲亚砜等;植物油诸如大豆油、油菜籽油、棉籽油、蓖麻油等;水等。这些可以单独使用,或使用其中2种或更多种的混合物。
要用作分散剂或润湿剂的表面活性剂的例子包括:非离子型表面活性剂诸如脂肪酸的脱水山梨糖醇酯、脂肪酸的聚氧乙烯脱水山梨糖醇酯、脂肪酸的蔗糖酯、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、聚氧苯乙烯-聚氧乙烯嵌段共聚物、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、聚氧乙烯脂肪酸联苯基醚、聚亚烷基苄基苯基醚、聚亚氧烷基苯乙烯基苯基醚、乙炔二醇、聚亚氧烷基加成乙炔二醇、聚氧乙烯醚型有机硅、酯型有机硅、氟表面活性剂、聚氧乙烯蓖麻油、氢化聚氧乙烯蓖麻油等;阴离子表面活性剂诸如烷基硫酸盐、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、萘磺酸甲醛缩合物的盐、烷基萘磺酸甲醛缩合物的盐、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;阳离子表面活性剂诸如月桂基胺盐酸盐、硬脂酰胺盐酸盐、油烯基胺盐酸盐、硬脂酰胺乙酸盐、硬脂酰氨基丙胺乙酸盐、烷基胺盐(包括烷基三甲基氯化铵和烷基二甲基苯扎氯铵)等;两性表面活性剂诸如氨基酸或甜菜碱表面活性剂等,等。这些表面活性剂可以单独使用,或使用其中2种或更多种的混合物。
粘合剂和增粘剂的例子包括:羧甲基纤维素或其盐、糊精、水溶性淀粉、黄原胶、瓜尔胶、蔗糖、聚乙烯吡咯烷酮、阿拉伯树胶、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸钠、具有6,000-20,000的平均分子量的聚乙二醇、具有100,000-5,000,000的平均分子量的聚氧化乙烯、磷脂(例如脑磷脂或卵磷脂)、纤维素粉末、糊精、经加工的淀粉、聚氨基羧酸螯合物化合物、交联的聚乙烯吡咯烷酮、马来酸-苯乙烯共聚物、(甲基)丙烯酸共聚物、多元醇和二羧酸酸酐形成的半酯、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、烷基酚甲醛缩合物和合成树脂乳剂等。
增稠剂的例子包括:水溶性的聚合物诸如黄原胶、瓜尔胶、迪特胶(diutan gum)、羧甲基纤维素、聚乙烯吡咯烷酮、羧基乙烯基聚合物、丙烯酸聚合物、淀粉衍生物和多糖;无机细粉诸如高纯度膨润土和烟雾硅胶(白炭墨)等。
着色剂的例子包括:无机颜料诸如氧化铁、氧化钛和普鲁士蓝;有机染料诸如茜素染料、偶氮染料和金属酞菁染料等。
防冻剂的例子包括:多元醇诸如乙二醇、二乙二醇、丙二醇、甘油等,等。
用于防止结块或促进崩解的辅助剂的例子包括:多糖(例如淀粉、海藻酸、甘露糖和半乳糖)、聚乙烯吡咯烷酮、烟雾硅胶(白炭墨)、酯树胶、石油树脂、三聚磷酸钠、六偏磷酸钠、金属硬脂酸盐、纤维素粉末、糊精、甲基丙烯酸酯共聚物、聚乙烯吡咯烷酮、聚氨基羧酸螯合物化合物、磺化苯乙烯-异丁烯-马来酸酐共聚物和淀粉-聚丙烯腈接枝共聚物等。
稳定剂的例子包括:干燥剂诸如沸石、生石灰和氧化镁;抗氧化剂诸如苯酚化合物、胺化合物、硫化合物、磷酸化合物等;紫外吸收剂诸如水杨酸化合物、二苯甲酮化合物等,等。
防腐剂的例子包括:山梨酸钾、1,2-苯并噻唑啉-3-酮等。
此外,如果必要,还可以使用功能性铺展剂、活性增强剂(如代谢分解抑制剂,如胡椒基丁醚)、防冻剂(如丙二醇)、抗氧化剂(如BHT)、紫外线吸收剂和其它助剂。
作为活性成分的化合物的含量可以根据需要改变,并且可以以在每100份0.01-90重量份本发明的农业园艺用试剂的范围内适当选择的比例使用作为活性成分的化合物。例如,在粉剂、颗粒剂、乳剂或可湿性粉剂中,作为活性成分的化合物的合适含量是0.01-50重量份(农业园艺用杀虫剂的总重量的0.01-50重量%)。
本发明的农业园艺用杀虫剂的施用量随多种因素变化,所述因素是例如目的、要防治的害虫、植物的生长状态、害虫出现的趋势、气候、环境条件、剂型、施用方法、施用部位和施用时间。其可以根据目的在0.001g至10 kg、优选0.01克至1kg(就作为活性成分的化合物而言)/10公亩的范围内适当地选择。
本发明的农业园艺用杀虫剂可以与其它农业园艺用杀虫剂、杀螨剂、杀线虫剂、杀真菌剂、生物杀虫剂等混合使用以拓宽可防治病害虫的范围和有效施用的时间周期或减少剂量。此外,本发明的农业园艺用杀虫剂可以根据应用情形与除草剂、植物生长调节剂、肥料等混合使用。
要用于这样的目的其它的农业园艺用杀虫剂、杀螨剂和杀线虫剂的例子包括:甲基氨基甲酸-3,5-二甲苯酯(灭除威),由苏云金芽孢杆菌鲇泽亚种(Bacillusthuringienses aizawai)、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensesisraelensis)、苏云金芽孢杆菌日本亚种(Bacillus thuringienses japonensis)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringienses kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringienses tenebrionis)、苏云金芽孢杆菌(Bacillusthuringienses)生成的晶体蛋白毒素,BPMC,Bt毒素杀虫剂化合物,CPCBS (杀螨酯),二氯异丙醚(二氯二异丙基醚),D-D (1,3-二氯丙烯),滴滴涕,NAC,O,O-二乙基硫代磷酸-O-4-二甲基氨磺酰基苯酯(DSP),苯基硫代膦酸- O-乙基O-4-硝基苯基酯(苯硫磷),异氰脲酸三丙酯(TPIC),氟丙菊酯,印楝素,保棉磷,灭螨醌,啶虫脒,乙酰虫腈,乙酰甲胺磷,阿维菌素,阿维菌素-B,磺胺螨酯,双甲脒,棉铃威,涕灭威,涕灭砜威,艾氏剂,α-硫丹,顺式氯氰菊酯,丙硫多菌灵,烯丙菊酯,氯唑磷,isamidofos,isoamidofos,异噁唑磷,异柳磷,异丙威:MIPC,伊维菌素,imicyafos,吡虫啉,咪炔菊酯,茚虫威,高氰戊菊酯,乙硫苯威,乙硫磷,乙虫腈,乙螨唑,醚菊酯,丙线磷,乙嘧硫磷,依马菌素,依马菌素苯甲酸盐,硫丹,右旋烯炔菊酯,杀线威,亚砜磷,异亚砜磷:ESP,奥苯达唑,奥芬达唑,油酸钾,油酸钠,硫线磷,杀螟丹,甲萘威,丁硫克百威,克百威,精高效氯氟氰菊酯,灭杀威,喹硫磷,烯虫炔酯,灭螨猛,除线威,噻虫胺,四螨嗪,环虫酰肼,氯虫酰胺,氯氧磷,杀虫脒,氯丹,毒死蜱,甲基毒死蜱,溴虫清,杀螨酯,毒虫畏,定虫隆,乙酯杀螨醇,氯苯甲酸盐,三氯杀螨醇,水杨硫磷,杀螟腈:CYAP,杀螨隆,除线特,氰虫酰胺,高效反式氯氰菊酯,遍地克,腈吡螨酯,蔬果磷,苯虫醚,σ-氯氰菊酯,除线磷:ECP,乙氰菊酯,敌敌畏:DDVP,乙拌磷,呋虫胺,氯氟氰菊酯,苯醚氰菊酯,氟氯氰菊酯,除虫脲,丁氟螨酯,氟螨嗪,三环锡,氯氰菊酯,甲基毒虫畏,乐果,四氟甲醚菊酯,氟硅菊酯,灭蝇胺,乙基多杀菌素,多杀菌素,螺螨酯,螺虫乙酯,螺甲螨酯,氟虫胺,硫丙磷,砜虫啶,ζ-氯氰菊酯,二嗪磷,氟胺氰菊酯,棉隆,噻虫啉,噻虫嗪,硫双威,杀虫环,杀虫单,杀虫双,虫线磷,甲基乙拌磷,避蚊胺,狄氏剂,杀虫畏,三氯杀螨砜,四氟醚菊酯,胺菊酯,丁基嘧啶磷,虫酰肼,吡螨胺,七氟菊酯,氟苯脲,硫赶式甲基内吸磷,双硫磷,溴氰菊酯,特丁磷,溴代吡咯腈,四溴菊酯,四氟苯菊酯,唑蚜威,triazuron,水杨菌胺,敌百虫:DEP,杀铃脲,唑虫酰胺,三溴磷:BRP,硝虫噻嗪,烯啶虫胺,氟酰脲,多氟脲,烯虫乙酯,甲烯氟虫腈,蚜灭磷,对硫磷,对硫磷甲酯,苄螨醚,氯虫酰肼,双三氟虫脲,杀虫双,氟蚁腙,羟基丙基淀粉,乐杀螨,联苯肼酯,联苯菊酯,吡蚜酮,吡唑硫磷,吡嗪氟虫腈,哒嗪硫磷,哒螨灵,啶虫丙醚,氟虫吡喹,吡啶氟虫腈,吡丙醚,抗蚜威,嘧螨醚,甲基嘧啶磷,除虫菊素,氟虫腈,喹螨醚,苯线磷,溴螨酯,杀螟硫磷:MEP,苯氧威,苯硫威,苯醚菊酯,仲丁威,丰索磷,倍硫磷:MPP,稻丰散:PAP,氰戊菊酯,唑螨酯,甲氰菊酯,芬苯达唑,噻唑膦,伐虫脒,丁嘧硫磷,噻嗪酮,呋线威,炔酮菊酯,嘧螨酯,氟啶胺,啶蜱脲,氟噻虫砜,氟环脲,氟氰戊菊酯,氟胺氰菊酯,吡氟硫磷,嘧虫胺,氟虫脲,氟螨嗪,三氟醚菊酯,苄螨醚,溴氟菊酯,氟虫双酰胺,氟氯苯菊酯,flurimfen,丙硫磷,protrifenbute,氟啶虫酰胺,丙虫磷,快螨特:BPPS,丙溴磷,丙氟菊酯,残杀威:PHC,溴螨酯,高效氟氯氰菊酯,氟铃脲,噻螨酮,庚烯磷,氯菊酯,异噻虫唑,噁虫威,杀虫磺,苯螨特,丙硫克百威,辛硫磷,伏杀硫磷,噻唑膦,丁硫环磷,磷胺,磷虫威,亚胺硫磷PMP,多萘菌素,伐虫脒,安果磷,甲拌磷,机油,马拉硫磷,米尔倍霉素,米尔倍霉素-A,米尔蓓菌素,灭蚜蜱,甲亚砜磷,灭多威,四聚乙醛,氰氟虫腙,甲胺磷,威百亩-铵,威百亩,灭梭威,杀扑磷:DMTP,异硫氰酸甲酯,methylneodecanamide,甲基对硫磷,噁虫酮,甲氧氯,甲氧虫酰肼,甲氧苄氟菊酯,烯虫酯,速灭威,氯氟醚菊酯,速灭磷,久效磷,杀虫单,高效氯氟氰菊酯,兰尼碱,虱螨脲,苄呋菊酯,雷皮菌素,鱼藤酮,左旋咪唑盐酸盐,苯丁锡,酒石酸莫仑太尔,甲基溴,三环锡,氰氨化钙,多硫化钙,硫磺,硫酸烟碱等。
要用于上述相同目的的农业园艺用杀真菌剂的例子包括:土壤杀真菌剂诸如金色制霉素、氧环唑、塞仑、脂酸盐、acibenzolar、苯并噻二唑、腈嘧菌酯、敌菌灵、吲唑磺菌胺、氨丙磷酸、辛唑嘧菌胺、烯丙醇、十二吗啉、代森铵、异噻菌胺、isovaledione、萘吡菌胺、稻瘟灵、种菌唑、异菌脲、异丙菌胺、异稻瘟净、抑霉唑、双胍辛胺、iminoctadine-albesilate、双胍辛胺-三乙酸盐、酰胺唑、烯效唑、单克素、echlomezole、敌瘟磷、乙环唑、韩乐宁、乙嘧酚、代森硫、乙氧喹啉、土菌灵、烯肟菌酯、氟环唑、噁霜灵、氧化萎锈灵、8-羟基喹啉铜、土霉素、copper-oxinate、恶咪唑、恶咪唑-富马酸盐、喹菌酮、辛噻酮、呋酰胺、肟醚菌胺、威百亩等,春雷霉素、吗菌威、加普胺、多菌灵、萎锈灵、香芹酮、醌菌腙、喹烯酮、苯氧喹啉、灭螨猛、敌菌丹、克菌丹、精苯霜灵、氯苯喹唑、五氯硝基苯、双胍辛盐、硫杂灵、杀菌威、果绿定、灰荑霉素、咪菌酮、甲酚、醚菌酯、乙菌利、克霉唑、灭瘟唑、双胺灵、四氯对醌、四氯喹恶啉、氯化苦、苯咪唑菌、氯二硝基萘、百菌清、地茂散、氰菌胺、水杨酰苯胺、氰霜唑、焦碳酸二乙酯、乙霉威、环菌胺、双氯氰菌胺、菌核利、苄氯三唑醇、苯氟磺胺、放线菌酮、哒菌酮、氯硝胺、双氯酚、二氯萘醌、双硫仑、灭菌磷、二噻农、烯唑醇、R-烯唑醇、代森锌、消螨普、邻敌螨消、硝辛酯、硝丁酯、消螨通、硝戊酯、双硫氧吡啶、二苯基胺、噁醚唑、环氟菌胺、氟嘧菌胺、环丙唑醇、嘧菌环胺、酯菌胺、氰菌灵、硅氟唑、二甲嘧酚、烯酰吗啉、霜脲氰、醚菌胺、甲基溴、福美锌、硅噻菌胺、链霉素、螺噁茂胺、戊苯砜、环丙吡菌胺、苯酰菌胺、棉隆、噻二嗪、噻酰菌胺、氟噻亚菌胺、噻菌灵、tioxymid、thiochlorfenphim、硫菌灵、甲基硫菌灵、噻菌腈、克杀螨、灭螨猛、噻呋酰胺、福美双、癸磷锡、四氯硝基苯、叶枯酞、福美双联、氟醚唑、咪菌威、脱氢乙酸、戊唑醇、异丁乙氧喹啉、多地辛、多果定、十二烷基苯磺酸双乙二胺铜(II) (DBEDC)、十二环吗啉、肼菌酮、三唑醇、三唑酮、丁基三唑、咪唑嗪、威菌磷、嘧菌醇、水杨菌胺、三环唑、灭菌唑、十三吗啉、三丁基氧化锡、氟菌唑、肟菌酯、嗪氨灵、甲苯氟磺胺、甲基立枯磷、多马霉素、代森钠、酞菌酯、硝基苯乙烯、氟苯嘧啶醇、壬基苯酚磺酸铜、丙烯酸喹啉酯、有效霉素、霜霉灭、harpin蛋白、联苯吡菌胺、啶氧菌酯、氟吡菌胺、硫氯酚、联苯三唑醇、土菌消、土菌消钾、乐杀螨、联苯、病花灵、噁霉灵、唑菌酯、吡喃灵、唑菌胺酯、定菌磷、唑胺菌酯、甲氧苯啶菌、啶菌腈、啶斑肟、吡菌苯威、嘧霉胺、氯甲氧吡啶、氯吡呋醚、咯喹酮、乙烯菌核利、噁唑菌酮、咪菌腈、咪唑菌酮、敌克松、氯苯嘧啶醇、种衣酯、氰菌胺、嘧菌腙、福美铁、三苯锡、拌种咯、胺苯吡菌酮、腈苯唑、甲呋酰胺、苯锈啶、丁苯吗啉、环酰菌胺、四氯苯酞、丁硫丹、丁胺、乙嘧酚磺酸酯、麦穗宁、灭瘟素、呋吡菌胺、呋霜灵、嘧螨酯、氟啶胺、氟嘧菌酯、三氟苯唑、氟吡菌胺、氟吡菌酰胺、氟氯菌核利、二甲呋酰胺、氟唑菌酰胺、氟喹唑、呋菌唑、呋醚唑、咯菌腈、氟硅唑、磺菌胺、氟噻亚菌胺、氟酰胺、粉唑醇、糠醛、茂谷乐、氟酰菌胺、氟吗啉、丙氧喹啉、咪鲜胺、腐霉利、硫菌威、丙硫菌唑、霜霉威、丙环唑、丙森锌、呋菌隆、烯丙苯噻唑、糠菌唑、六氯丁二烯、己唑醇、环己硫磷、哒菌酮、苯霜灵、精苯霜灵、麦锈灵、苯菌灵、稻瘟酯、醌肟腙、配那唑、抑菌啉、戊菌隆、苯甲羟肟酸、bentaluron、苯噻清、苯噻菌胺酯、吡噻菌胺、戊苯吡菌胺、啶酰菌胺、氯瘟磷、三乙膦酸、三乙膦酸铝、多抗霉素、多氧霉素、代森福美锌、灭菌丹、甲醛、机油、代森锰、代森锰锌、双炔酰菌胺、甲菌利、腈菌唑、米多霉素、代森环、苯并威、磺菌威、间氯敌菌酮、威百亩、威百亩、甲霜灵、精甲霜灵、代森联、异硫氰酸甲酯、mepthyldinocap、叶菌唑、噻菌胺、灭菌胺、苯氧菌胺、苯菌酮、嘧菌胺、精甲霜灵、消螨多、灭锈胺、灭锈胺、碘甲烷、吡咪唑、苯扎氯铵、碱式氯化铜,无机抗微生物剂诸如碱式硫酸铜、银等、次氯酸钠、氢氧化铜、可湿性硫、多硫化钙、碳酸氢钾、碳酸氢钠、硫磺、无水硫酸铜、福美镍,铜化合物诸如喹啉铜、硫酸锌、五水合硫酸铜等。
类似地,除草剂的例子包括:1-萘基乙酰胺、2,4-PA、2,3,6-TBA、2,4,5-涕、2,4,5-涕丁酸、2,4-滴、2,4-滴丁酸、2,4-DEB、2,4-DEP、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、MCP、2-甲基-4-氯苯氧乙酸(MCPA)、2-甲基-4-氯苯氧乙酸硫代乙酯(MCPAthioethyl)、2甲4氯丁酸(MCPB)、碘苯腈、苯草醚、唑啶炔草、三氟羧草醚、叠氮净、四唑嘧磺隆、磺草灵、乙草胺、莠去津、阿特拉通、疏草隆、莎稗磷、四烯雌酮、脱落酸、氨唑草酮、酰嘧磺隆、杀草强、环丙嘧啶酸、氯氨基吡啶酸、特草嗪酮、甲基胺草磷、特津酮、莠灭净、甲草胺、二丙烯草胺、禾草灭、五氯戊酮酸、异噁隆、草特灵、异噁氯草酮、异噁草醚、异噁唑草酮、异噁酰草胺、异草定、异草完隆、异丙隆、异丙乐灵、isopolinate、丁嗪草酮、抗倒胺、抑草津、卤苯胺唑、丙草定、灭草喹、甲基咪草烟、灭草烟、imazamethapyr、咪草酸、咪草酸、咪草啶酸、咪草烟、唑吡嘧磺隆、三嗪茚草胺、茚草酮、吲哚丁酸、单克素、甘草津、禾草畏、胺苯磺隆、甲基胺苯磺隆、乙丁烯氟灵、硫草敌、吲熟酯、磺噻隆、硝草酚、乙烯利、乙氧嘧磺隆、氯氟草醚、乙胺草醚、乙氧呋草黄、乙氧苯酰草、磺唑草、抑草蓬、茵多酸、噁草酮、炔丙噁唑草、氯噁嗪草、环丙氧磺隆、草哒松、乙氧氟草醚、消草磺灵、嘧苯胺磺隆、坪草丹、唑草胺、克草胺酯、卡巴草灵、唑草酮、唑草酮乙酯、特胺灵、双酰草胺、特噁唑威、喹禾灵、精喹禾灵、禾草克、二甲苯草胺、灭藻醌、氯藻胺、二氯喹啉酸、氯甲喹啉酸、苄草隆、碘氯啶酯、草甘膦、草铵膦、草铵膦-P、醚草敏、烯草酮、座果酸、炔草酸、炔草酯、氯麦隆、二氯吡啶酸、环丁烯草酮、调果酸、氯溴隆、氯丁草、异恶草松、氯硝醚、甲氧除草醚、氯甲酰草胺、炔禾灵、可乐津、氯酯磺草胺、丁酰草胺、草灭喂、氯酯磺草胺甲酯、氯草敏、氯嘧磺隆、氯嘧磺隆、氯磺隆、敌草索、草克乐、绿麦隆、草枯醚、伐草克、燕麦酯、氯草灵、氟嘧杀、整形醇、草败死、氯普芬、矮壮素、乙氧苯隆、羟敌草腈、枯草隆、三氯丙酸、苯嘧磺草胺、氰草津、氰草净、燕麦敌、敌草隆、二乙除草双、麦草畏、环莠隆、环草敌、噻草酮、双氯磺草胺、环丙磺隆、2,4-滴丙酸、精2,4-滴丙酸、敌草腈、禾草灵、禾草灵、二氯苄草酯、氯全隆、敌草快、咯草隆、disul、环草隆、氟硫草定、敌乐胺、吲哚酮草酯、戊硝酚、醚磺隆、地乐酚、特乐酚、地乐特、丙硝酚、氰氟草酯、草乃敌、枯莠隆、氟苯戊烯酸、野燕枯、cybutryne、环丙津、三环塞草胺、吡氟酰草胺、氟吡草腙、异丙净、环丙草胺、牧草快、赤霉素、西玛津、草灭散、二甲草胺、敌米达松、异戊乙净、二甲吩草胺、西草净、西玛通、哌草丹、噁唑隆、环庚草醚、灭草灵、吖庚磺酯、磺草酮、菜草畏、甲磺草胺、磺酰磺隆、甲嘧磺隆、甲嘧磺隆、密草通、烯禾啶、另丁津、特草定、杀草隆、棉隆、茅草枯、噻氟隆、噻草啶、噻酮磺隆、噻酮磺隆、仲草丹、嘧草胺、禾草丹、噻二唑胺、噻苯隆、噻吩磺隆、噻吩磺隆、甜菜安、敌草净、氟氧隆、噻吩草胺、牧草胺、丁噻隆、甲氧去草净、吡喃草酮、特呋三酮、环磺酮、异丁草胺、特草定、特草灵、特丁草胺、特丁津、特丁净、苯吡唑草酮、三甲苯草酮、三嗪氟草胺、醚苯磺隆、野麦畏、草达津、杀草畏、定草酯、灭草环、草达克、三氟甲磺隆、氟胺磺隆、氟胺磺隆、氟乐灵、三氟啶磺隆、茚草酮、苯磺隆、苯磺隆、三氟苯氧丙酸、三氟禾草肟、三甲隆、萘草胺、萘丙胺、敌草胺、烟嘧磺隆、磺乐灵、除草醚、三氟甲草醚、吡氯草胺、草不隆、哒草伏、草完隆、燕麦灵、多效唑、百草枯、对氟隆、卤草定、氟吡甲禾灵、高效氟吡甲禾灵、氟吡甲禾灵甲酯、氟硝磺酰胺、氯吡嘧磺隆、氯吡嘧磺隆、毒莠定、氟吡酰草胺、二环吡草酮、双草醚、双草醚-钠、比达农、唑啉草酯、甲羧除草醚、哌草磷、噁霉灵、双唑草腈、磺酰草吡唑、苄草唑、吡嘧磺隆、吡嘧磺隆、吡唑特、双丙氨酰磷、吡草醚-乙酯、氯草定、pyridafol、嘧硫草醚、嘧草硫醚、哒草特、环酯草醚、稗草畏、嘧苯草肟、吡丙醚、氟嘧磺隆、嘧草醚、pyroxasulfone、甲氧磺草胺、酰苯磺威、棉胺宁、非草隆、异噁苯砜、噁唑禾草灵、精噁唑禾草灵、噁唑禾草灵、酚硫杀、2,4,5-涕丙酸、苯酰敌草隆、噻唑禾草灵、氯苯氧乙醇、四唑草胺、甜菜宁、甜菜宁-乙酯、丁草胺、氟丙嘧草酯、抑草磷、丁噻隆、特咪唑草、丁草敌、播土隆、丁烯草胺、丁苯草酮、仲丁灵、啶嘧磺隆、麦草伏、呋氧草醚、丙炔草胺、氟嘧磺隆、吡氟禾草灵、精吡氟禾草灵、吡氟禾草灵、异丙吡草酯、氯氟吡氧乙酸、氟硫隆、伏草隆、乙羧氟草醚、氟咯草酮、三氟硝草醚、氟除草醚、唑啶草、氟酮磺隆、氟酮磺隆钠、氟消草、氟吡磺隆、达草氟、氟噻甲草酯、氟啶磺隆、氟噻草胺、氟苯吡草、氟哒嗪草酯、氟单丙嘧草酯、四氟丙酸、氟胺草唑、丙炔氟草胺、氟烯草酸、氟烯草酸、炔草胺、三氟噁嗪、伏草隆、唑嘧磺草胺、氟啶草酮、呋草酮、氯氟吡氧乙酸、丙草胺、黄原酸异丙酯、甘扑津、环丙青津、氨氟乐灵、甲硫磺乐灵、氟磺隆、苄草丹、恶草酸、毒草胺、扑灭津、敌稗、炔苯酰草胺、异丙草胺、茉莉酮、嗪咪唑嘧磺隆、苯胺灵、氟唑草胺、环丙氟灵、调环酸钙、丙苯磺隆、丙苯磺隆钠、环苯草酮、除草定、溴莠敏、扑草净、扑灭通、溴苯腈、溴酚肟、溴丁酰草胺、糠草腈、双氟磺草胺、六氯丙酮、环嗪酮、烯草胺、草除灵、五氟磺草胺、克草敌、氟丁酰草胺、灭草敌、黄草伏、酰苯草酮、胺酸杀、苄草胺、苄基氨基嘌呤、苯噻隆、双苯嘧草酮、地散磷、苄嘧磺隆、新燕灵、苯并双环酮、吡草酮、氟磺胺草、灭草松、戊酰苯草胺、禾草丹、二甲戊灵、戊噁唑草、乙丁氟灵、呋草黄、杀木膦、氟磺胺草醚、甲酰胺磺隆、调吡脲、抑芽丹、2甲4氯丙酸、精2甲4氯丙酸、地乐施、甲基二磺隆、甲磺胺磺隆、甲基磺草酮、灭莠津、甲氧丙净、吡草胺、灭草唑、双醚氯吡嘧磺隆、甲基苯噻隆、苯嗪草酮、噁唑酰草胺、威百亩、氟烯硝草、灭草恒、噁噻草醚、甲硫苯威、甲基杀草隆、甲氧隆、磺草唑胺、甲磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、二甲哒草伏、溴谷隆、吡喃隆、醚草通、异丙甲草胺、嗪草酮、甲哌鎓、苯噻酰草胺、氟磺酰草胺、庚酰草胺、monisouron、灭草隆、一氯乙酸、绿谷隆、草达灭、伐草快、碘磺隆、碘甲磺隆钠、碘草腈、碘甲烷、乳氟禾草灵、利谷隆、砜嘧磺隆、环草定、硫氰苯乙胺、过氧化钙、甲基溴等。
至于生物杀虫剂,通过将本发明的农业园艺用试剂与例如下述物质混合使用可以预见到与以上相同的效果:从核型多角体病毒(NPV)、颗粒体症病毒(GV)、质型多角体病病毒(CPV)、昆虫痘病毒(EPV)等获得的病毒制剂;用作杀虫剂或杀线虫剂的微生物杀虫剂,诸如瘤捕单顶孢(Monacrosporium phymatophagum)、小卷蛾斯氏线虫(Steinernema carpocapsae)、Steinernema kushidai、侵入巴斯德氏芽菌(Pasteuria penetrans)等;用作杀真菌剂的微生物杀虫剂,诸如木素木霉(Trichoderma lignorum)、放射形土壤杆菌(Agrobacterium radiobacter)、非病原性的胡萝卜软腐欧文氏菌(Erwinia carotovora)、枯草芽孢杆菌(Bacillus subtilis)等;和用作除草剂的生物杀虫剂诸如野油菜黄单胞菌(Xanthomonas campestris)等。
另外,本发明的农业园艺用试剂可以与生物杀虫剂联合使用,所述生物杀虫剂包括天敌,诸如寄生蜂(丽蚜小蜂(Encarsia formosa))、寄生蜂(阿布拉小蜂(Aphidius colemani))、瘿蚊(食蚜瘿蚊(Aphidoletes aphidimyza))、寄生蜂(潜蝇姬小蜂(Diglyphus isaea))、寄生螨(离颚茧蜂(Dacnusa sibirica))、捕食性螨(智利小植绥螨(Phytoseiulus persimilis))、捕食性螨(胡瓜钝绥螨(Amblyseius cucumeris))、捕食性蝽(东亚小花蝽(Orius sauteri))等;微生物杀虫剂诸如布氏白僵菌,(Beauveria brongniartii)等;和信息素诸如乙酸-(Z)-10-十四烯酯、乙酸-(E,Z)-4,10-十四碳二烯酯、乙酸-(Z)-8-十二烯酯、乙酸-(Z)-11-十四烯酯、(Z)-13-二十碳烯-10-酮、14-甲基-1-十八碳烯等。
下面显示了本发明的代表性实施例,所述实施例不应解释为限制性的。
参考实施例1-1。
5-丁基-4-羟基嘧啶的生产
在氩气氛下在5-10℃向甲醇钠(8.3 g, 154 mmol)在无水四氢呋喃(40 mL)中的溶液中,接连地逐滴加入甲酸乙酯(7.4 g, 100 mmol)和己酸甲酯(10 g, 77 mmol),并将混合物在室温搅拌3小时。向反应溶液中逐滴加入醋酸甲脒(8.0 g, 77 mmol)在甲醇(70mL)中的溶液和28%的甲醇钠在甲醇中的溶液(16 g, 81 mmol),并将混合物在回流下加热搅拌10小时。将反应溶液冷却至室温,加入水(10 mL)以溶解沉淀的盐,并将混合物在减压下浓缩。加入浓盐酸(15 mL),并将混合物用乙酸乙酯萃取。将有机层经无水硫酸镁干燥,在减压下浓缩,并通过硅胶柱色谱法纯化,得到5-正丁基-4-羟基嘧啶(1.3 g, 11%)。
收率:11%
性质:1H-NMR (400MHz, CDCl3): δ8.05 (s, 1H), 7.85 (s, 1H), 2.50 (t,2H), 1.65-1.66 (m, 2H), 1.45-1.35 (m, 2H), 0.95 (t, 3H)。
参考实施例1-2。
5-丁基-4-氯嘧啶的生产
向在前述生产方法中生产的5-丁基-4-羟基嘧啶(1.3 g, 8.5 mmol)在甲苯(5mL)中的溶液中,加入磷酰氯(3.9 g, 26 mmol),并将混合物在回流下加热搅拌2小时。将混合物冷却至室温,并在减压下浓缩以除去多余的磷酰氯。将残余物倒入饱和碳酸氢钠水溶液中,并将混合物用MTBE萃取。将有机层经无水硫酸镁干燥,并在减压下浓缩,得到作为粗制纯化产物的5-丁基-4-氯嘧啶(1.1 g, 76%)。
收率:76%
性质:1H-NMR (400MHz, CDCl3):δ8.84 (s, 1H), 8.51 (s, 1H), 2.72 (t, 2H),1.70-1.60 (m, 2H), 1.50-1.40 (m, 2H), 0.98 (t, 3H)。
实施例1。
5-丁基-4-(4-叔丁基苄氧基)嘧啶(化合物编号1-7)的生产
在0℃向在前述生产方法中生产的5-丁基-4-氯嘧啶(0.20 g, 1.2 mmol)和4-叔丁基苯甲醇(0.19 g, 1.2 mmol)在THF (5 mL)中的溶液中加入氢化钠(0.051 g, 1.3mmol),并将混合物在室温搅拌3小时。将反应混合物倒入冰水中,并将混合物用乙酸乙酯萃取。将有机层经无水硫酸镁干燥,并在减压下浓缩溶剂。通过硅胶柱色谱法纯化残余物,得到5-丁基-4-(4-叔丁基苄氧基)嘧啶(0.26 g, 74%)。
收率:74%
性质:1.5360 (27.5℃)。
参考实施例2-1。
4,6-二氯-5-(1,3-二氧杂环戊烷-2-基)嘧啶的生产
在室温向参考WO2001/017975合成的4,6-二氯-5-甲酰基嘧啶(10 g, 56.5 mmol)在甲苯(60 ml)中的溶液中,加入对甲苯磺酸(1 g, 5.65 mmol)和乙二醇(7 g, 113mmol),并将混合物在回流下共沸地加热搅拌30 min。向反应溶液中加入乙酸乙酯,并将混合物用饱和碳酸氢钠水溶液和饱和盐水洗涤。将有机层经无水硫酸镁干燥,并在减压下浓缩。通过硅胶柱色谱法纯化残余物,得到4,6-二氯-5-(1,3-二氧杂环戊烷-2-基)嘧啶(8.4g)。
收率:67%
性质:1H-NMR (400MHz, CDCl3):δ8.75 (s, 1H), 6.37 (s, 1H), 4.28-4.37 (m,2H), 4.06-4.15 (m, 2H)。
参考实施例2-2。
6-氯-4-(4-三氟甲基苄氧基)-5-(1,3-二氧杂环戊烷-2-基)嘧啶的生产
在0℃向4,6-二氯-5-(1,3-二氧杂环戊烷-2-基)嘧啶(2.0 g, 9.1 mmol)和4-三氟甲基苯甲醇(1.8 g, 10 mmol)在DMA (10 mL)中的溶液中加入氢化钠(0.43 g, 11mmol),并将混合物在室温搅拌3小时。将反应混合物倒入冰水中,并将混合物用乙酸乙酯萃取。将有机层经无水硫酸镁干燥,并在减压下浓缩溶剂。通过硅胶柱色谱法纯化残余物,得到6-氯-4-(4-三氟甲基苄氧基)-5-(1,3-二氧杂环戊烷-2-基)嘧啶(2.2 g, 67%)。
收率:67%
性质:1H-NMR (400MHz, CDCl3):δ8.53 (s, 1H), 7.64 (d, 2H), 7.53 (d, 2H),6.34(s, 1H), 4.15-4.10 (m, 2H), 4.05-3.95 (m, 2H)。
实施例2。
4-(4-三氟甲基苄氧基)-5-(1,3-二氧杂环戊烷-2-基)嘧啶(化合物编号4-4)的生产
在氩气氛下,向6-氯-4-(4-三氟甲基苄氧基)-5-(2-二氧杂环戊烷基)嘧啶(2.2g, 6.1 mmol)在DMA (10mL)中的溶液中,加入三乙胺(1.0 g, 10 mmol)、甲酸(0.42 g,9.1 mmol)和四(三苯基膦)钯(0.70 g, 0.61 mmol),并将混合物在80℃搅拌3小时。向反应溶液中加入水,并将混合物用叔丁基甲基醚萃取。将有机层用水和饱和盐水洗涤,并经无水硫酸镁干燥,并在减压下浓缩。通过硅胶柱色谱法纯化残余物,得到4-(4-三氟甲基苄氧基)-5-(1,3-二氧杂环戊烷-2-基)嘧啶(0.47 g, 24%)。
收率:24%
性质:38-39℃。
在下面显示了制剂实施例,它们不限制本发明。在制剂实施例中,份是指重量份。
制剂实施例1。
本发明的化合物 10份
二甲苯 70份
N-甲基吡咯烷酮 10份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 10份。
通过均匀地混合以上成分以实现溶解,制备可乳化浓缩剂。
制剂实施例2。
本发明的化合物 3份
粘土粉末 82份
硅藻土粉末 15份。
通过均匀地混合和碾磨以上成分,制备粉剂。
制剂实施例3。
本发明的化合物 5份
混合的膨润土和粘土的粉末 90份
木质素磺酸钙 5份。
通过均匀地混合以上成分,并将得到的混合物与合适量的水一起捏合,随后制粒和干燥,制备颗粒剂。
制剂实施例4。
本发明的化合物 20份
高岭土和合成的高分散硅酸的混合物 75份
聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物 5份。
通过均匀地混合和碾磨以上成分,制备可湿性粉剂。
实验实施例1。
对桃蚜(Myzus persicae)的防治效力
将大白菜植株植入每个塑料盆中,所述塑料盆具有8 cm的直径和8 cm的高度,并使桃蚜在植株上繁殖,此后计数每个盆中的蚜虫。将每种本发明的通式(I)的芳基烷氧基嘧啶衍生物或其盐分散在水中并用水稀释,以得到500 ppm液体化学制品。用所述液体化学制品喷洒盆栽的大白菜植株的茎和叶并风干,然后将所述盆储存在温室中。喷洒以后6天,计数在每个大白菜植株上的桃蚜寄生虫,并通过下述方程式计算防治效力程度,其中根据下面显示的标准来判断杀虫效果。
防治效力= 100 - {(T x Ca)/(Ta x C)}x 100
Ta:处理组中喷洒之前寄生虫的数目,
T:处理组中喷洒之后寄生虫的数目,
Ca:未处理组中喷洒之前寄生虫的数目,
C:未处理组中喷洒之后寄生虫的数目。
A防治效力100%
B防治效力99%- 90%
C防治效力89%- 80%
D防治效力79%- 50%。
实验实施例2。
对褐色稻飞虱(Nilaparvata lugens)的杀虫效果
将每种本发明的通式(I)的芳基烷氧基嘧啶衍生物或其盐分散在水中并用水稀释,以得到500 ppm液体化学制品。将稻幼苗(品种: Nihonbare)在所述液体化学制品中浸渍30秒并风干,此后将每株幼苗置于玻璃试管中,并接种10个褐色稻飞虱的第三龄期若虫,并用棉花塞塞紧试管。接种后8天,计数死亡率和存活率。通过下述方程式计算经校正的死亡率,并根据下述标准来判断防治效应。
诊断标准... 与实验实施例1相同。
结果,在实验实施例1中,在由式(I)表示的本发明的芳基烷氧基嘧啶衍生物中,化合物编号
和15-114的化合物对桃蚜表现出不小于D的杀虫效果,
且具体地,化合物
和15-114表现出A的优良杀虫效果。
另外,在实验实施例2中,在由式(I)表示的本发明的芳基烷氧基嘧啶衍生物中,化合物编号
和15-114的化合物对褐色稻飞虱表现出不小于D的杀虫效果,
且具体地,化合物
和15-114表现出A的优良杀虫效果。
实验实施例3. 对牛蜱(Haemaphysalis longicornis)的杀螨效果
将吸收棉置于玻璃瓶子(直径3 cm x高度4.5 cm)的底部。将由式(I)表示的本发明的芳基烷氧基嘧啶衍生物或其盐分散于水中,以得到稀释的药物溶液(200 ppm)。逐滴加入药物溶液(2 ml)。给每瓶接种5只牛蜱,并用网盖在瓶子上。从接种起4天后,计数死蜱和活蜱,并用下式计算经校正的死亡率,并根据实验实施例1的标准来判断杀螨效应。
经校正的死亡率(%)=(未处理组中的存活率-处理组中的存活率)/(未处理组中的存活率)×100。
结果,在由式(I)表示的本发明的芳基烷氧基嘧啶衍生物中,化合物编号1-2、2-5、2-37、2-54、3-21、3-111、4-19、4-41、4-53、4-67、8-22、8-26、9-45、10-7和15-78的化合物对牛蜱表现出不小于D的杀螨效应,且具体地,化合物1-2、2-5、2-54、3-21、3-111、4-67、9-45和15-78显示出A的优良杀螨效应。
工业适用性
本发明的芳基烷氧基嘧啶衍生物或其盐作为农业园艺用杀虫剂具有优良的作用。另一方面,所述衍生物对寄生在宠物动物(诸如狗和猫)和家养动物(诸如牛、绵羊等)中的害虫显示出作用。
本申请是基于在日本提交的专利申请号019768/2012和171532/2012,其内容特此通过引用并入。
Claims (8)
1.由式(I)表示的芳基烷氧基嘧啶衍生物或其盐,
其中,
R1是
(a124)以下结构式Q7、Q8或Q9,
其中R6和R7可以相同或不同,且各自为氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基(C1-C6)烷基、卤代(C1-C6)烷基、卤代(C3-C6)环烷基、卤代(C2-C6)烯基、卤代(C2-C6)炔基、卤代(C3-C6)环烷基(C1-C6)烷基、(C1-C6)烷基碳酰氧基(C1-C6)烷基、(C1-C6)烷氧基(C1-C6)烷基、羟基(C1-C6)烷基、(C2-C6)烯基氧基(C1-C6)烷基、苯氧基(C1-C6)烷基、(C1-C6)烷基磺酰基(C1-C6)烷基、(C1-C6)烷基磺酰氧基(C1-C6)烷基、卤素原子、苯基、苯基(C1-C6)烷基或(C1-C6)烷基羰基,
p是0-5的整数,且Z1和Z2可以相同或不同,且各自为CH2、氧原子、S、SO、SO2或NR6,其中R6如上面所定义,
R2和R3为
(b1)氢原子,
X可以相同或不同,且各自为
(c1)氢原子;
(c2)卤素原子;
(c4)氰基;
(c5)硝基;
(c14) (C1-C8)烷基;
(c18)卤代(C1-C8)烷基;
(c22)三(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c27) (C1-C8)烷氧基;
(c31)卤代(C1-C8)烷氧基;
(c40)卤代(C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c42) (C1-C8)烷硫基;
(c46)卤代(C1-C8)烷硫基;
q是1,
Y是CH,m是0-2的整数,n是0或1的整数。
2.根据权利要求1所述的芳基烷氧基嘧啶衍生物或其盐,其中Z1和Z2是氧原子。
3.一种农业园艺用杀虫剂,其包含根据权利要求1或2所述的芳基烷氧基嘧啶衍生物或其盐作为活性成分。
4.使用农业园艺用杀虫剂的方法,所述方法包括:用根据权利要求1或2所述的芳基烷氧基嘧啶衍生物或其盐处理植物或土壤。
5.一种防治农业园艺害虫的方法,所述方法包括:用根据权利要求1或2所述的芳基烷氧基嘧啶衍生物或其盐处理植物或土壤。
6.根据权利要求1或2所述的芳基烷氧基嘧啶衍生物或其盐作为农业园艺用杀虫剂的用途。
7.根据权利要求1或2所述的芳基烷氧基嘧啶衍生物或其盐在制造兽用杀虫剂中的用途。
8.由式(II)表示的芳基烷氧基嘧啶衍生物或其盐:
其中R1是
(a124)以下结构式Q7、Q8或Q9
其中R6和R7可以相同或不同,且各自为氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基(C1-C6)烷基、卤代(C1-C6)烷基、卤代(C3-C6)环烷基、卤代(C2-C6)烯基、卤代(C2-C6)炔基、卤代(C3-C6)环烷基(C1-C6)烷基、(C1-C6)烷基碳酰氧基(C1-C6)烷基、(C1-C6)烷氧基(C1-C6)烷基、羟基(C1-C6)烷基、(C2-C6)烯基氧基(C1-C6)烷基、苯氧基(C1-C6)烷基、(C1-C6)烷基磺酰基(C1-C6)烷基、(C1-C6)烷基磺酰氧基(C1-C6)烷基、卤素原子、苯基、苯基(C1-C6)烷基或(C1-C6)烷基羰基,
p是0-5的整数,且Z1和Z2可以相同或不同,且各自为CH2、氧原子、S、SO、SO2或NR6,其中R6如上面所定义,
R2和R3为
(b1)氢原子;
q是1,
X可以相同或不同,且各自为
(c1)氢原子;
(c2)卤素原子;
(c4)氰基;
(c5)硝基;
(c14) (C1-C8)烷基;
(c18)卤代(C1-C8)烷基;
(c22)三(C1-C8)烷基甲硅烷基,其中所述烷基可以相同或不同;
(c27) (C1-C8)烷氧基;
(c31)卤代(C1-C8)烷氧基;
(c40)卤代(C1-C8)烷氧基卤代(C1-C8)烷氧基;
(c42) (C1-C8)烷硫基;
(c46)卤代(C1-C8)烷硫基;
Y是CH,m是0-2的整数,和Hal是卤素原子。
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PCT/JP2013/052421 WO2013115391A1 (ja) | 2012-02-01 | 2013-02-01 | アリールアルキルオキシピリミジン誘導体及び該誘導体を有効成分として含有する農園芸用殺虫剤並びにその使用方法 |
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- 2013-02-01 WO PCT/JP2013/052421 patent/WO2013115391A1/ja active Application Filing
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Also Published As
Publication number | Publication date |
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MX362863B (es) | 2019-02-19 |
JP6147196B2 (ja) | 2017-06-14 |
MY166820A (en) | 2018-07-23 |
WO2013115391A1 (ja) | 2013-08-08 |
ZA201405673B (en) | 2015-10-28 |
MX2014009310A (es) | 2014-10-14 |
EP2810939A4 (en) | 2015-08-12 |
US9750252B2 (en) | 2017-09-05 |
KR101648285B1 (ko) | 2016-08-12 |
AU2013215867B2 (en) | 2017-02-02 |
TWI566701B (zh) | 2017-01-21 |
BR112014019099A8 (pt) | 2017-07-11 |
UY34605A (es) | 2013-09-02 |
PH12014501680B1 (en) | 2014-11-10 |
US20150005257A1 (en) | 2015-01-01 |
AU2013215867A1 (en) | 2014-08-21 |
JPWO2013115391A1 (ja) | 2015-05-11 |
AR089871A1 (es) | 2014-09-24 |
EP2810939B1 (en) | 2018-12-26 |
CN104185628A (zh) | 2014-12-03 |
BR112014019099B1 (pt) | 2019-04-02 |
BR112014019099A2 (zh) | 2017-06-20 |
PH12014501680A1 (en) | 2014-11-10 |
IN2014KN01680A (zh) | 2015-10-23 |
EP2810939A1 (en) | 2014-12-10 |
KR20140117680A (ko) | 2014-10-07 |
TW201338705A (zh) | 2013-10-01 |
CA2863003C (en) | 2017-12-12 |
CA2863003A1 (en) | 2013-08-08 |
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