CN115135384A - 苯并咪唑化合物或其盐类、和含有该化合物的农艺和园艺用杀虫杀螨剂以及其使用方法 - Google Patents
苯并咪唑化合物或其盐类、和含有该化合物的农艺和园艺用杀虫杀螨剂以及其使用方法 Download PDFInfo
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- CN115135384A CN115135384A CN202080082709.4A CN202080082709A CN115135384A CN 115135384 A CN115135384 A CN 115135384A CN 202080082709 A CN202080082709 A CN 202080082709A CN 115135384 A CN115135384 A CN 115135384A
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- alkyl
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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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
- A01N43/48—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
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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
- A01N43/64—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
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/02—Acaricides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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- A—HUMAN NECESSITIES
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Abstract
Description
[技术领域]
本发明涉及以苯并咪唑化合物或其盐类为有效成分的农艺和园艺用杀虫杀螨剂以及其使用方法。
[背景技术]
迄今为止,报道了某些苯并咪唑化合物可用作杀虫剂或医药等(例如参照专利文献1~4)。在这样的文献中,没有记载:在1位氮原子具有烷基磺酰基等磺酰基,并且含氮杂环的氮原子键合于2位的苯并咪唑化合物和杀虫效果。
[现有技术文献]
[专利文献]
[专利文献1]国际公开第2012/086848号小册子
[专利文献2]国际公开第2013/018928号小册子
[专利文献3]国际公开第2009/134750号小册子
[专利文献4]DE3824658号广报
[发明内容]
[发明所解决的技术问题]
在农业和园艺等作物生产中,害虫等导致的危害现在仍很大,从针对现有药物的耐药性害虫的产生、对于环境生物的影响、操作的省力化等观点出发,期望开发出:具有新的作用性,对于天敌益虫的影响较少,具有侵袭性等的农艺和园艺用杀虫杀螨剂。
[解决问题的技术手段]
本发明人等为了解决所述的问题而进行了深入研究,结果发现:通式(1)表示的在2位键合含氮杂环基的氮原子,在1位具有特定的磺酰基的苯并咪唑化合物或其盐类,不仅对于农艺和园艺用害虫类具有优异的防治效果,并且能够解决所述问题,从而完成了本发明。
即,本发明涉及一种苯并咪唑化合物或其盐类,其由下述化学式1表示,
[1]通式(1)
[化学式1]
式1中,R表示:
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C3-C6)环烷基(C1-C6)烷基;
(a4)卤代(C1-C6)烷基;
(a5)(C2-C6)烯基;或
(a6)(C2-C6)炔基,
Y1、Y2、Y3和Y4可以相同或不同,并且表示:
(b1)氢原子;
(b2)卤素原子;
(b3)(C1-C6)烷基;或
(b4)卤代(C1-C6)烷基,
Q选自以下的含氮5元环杂环基,
[化学式2]
式2中,X1和X4可以相同或不同,并且表示:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X2表示:
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)(C1-C12)烷基;
(d5)(C3-C6)环烷基;
(d6)(C2-C12)烯基;
(d7)(C2-C12)炔基;
(d8)(C1-C6)烷氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)(C1-C6)烷基硫基;
(d12)(C1-C6)烷基亚磺酰基;
(d13)(C1-C6)烷基磺酰基;
(d14)卤代(C1-C6)烷基硫基;
(d15)卤代(C1-C6)烷基亚磺酰基;
(d16)卤代(C1-C6)烷基磺酰基;
(d17)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d19)(C1-C6)烷基羰基;
(d20)(C1-C6)烷氧基羰基;
(d21)(C2-C6)炔氧基羰基;
(d22)(C1-C6)烷基硫基羰基;
(d23)(C1-C6)烷氧基羰基(C1-C6)烷基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d25)芳氧基(C1-C6)烷基;
(d26)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C1-C6)烷基;
(d27)芳氧基羰基;
(d28)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(d29)芳基羰基;
(d30)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基羰基;
(d31)芳基(C1-C6)烷基;
(d32)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(d33)芳基(C1-C6)烷氧基羰基;
(d34)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d37)R1R2N基,此处R1和R2可以相同或不同,并且表示:(aa)氢原子、(ab)(C1-C6)烷基、(ac)(C1-C6)烷氧基、(ad)(C1-C6)烷氧基羰基、(ae)(C1-C6)烷基磺酰基、(af)卤代(C1-C6)烷基磺酰基、(ag)芳基、(ah)(C3-C6)环烷基、(ai)卤代(C1-C6)烷基、(aj)芳基(C1-C6)烷基;
(d38)R1R2N羰基,此处R1和R2与上述相同;
(d39)R1R2N磺酰基,此处R1和R2与上述相同;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d44)(C3-C12)环烷基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d47)(C3-C6)环烷基(C1-C6)烷基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d51)(C1-C6)烷基羰氧基(C1-C6)烷基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基;
(d55)1-(C1-C6)烷氧基亚氨基(C1-C6)烷基;
(d56)(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d57)卤代(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d58)芳基(C1-C6)烷基硫基;或
(d59)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基硫基,
X3表示:
(e1)氢原子;
(e2)卤素原子;
(e3)(C1-C6)烷基;
(e4)卤代(C1-C6)烷基;
(e5)(C1-C6)烷氧基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e8)(C1-C6)烷基硫基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e10)(C1-C6)烷氧基羰基;
(e11)(C2-C6)炔氧基羰基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e14)芳基磺酰基;
(e15)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基磺酰基;
(e16)芳氧基羰基;
(e17)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(e18)芳基(C1-C6)烷氧基羰基;
(e19)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基;
(e20)芳基(C1-C6)烷氧基;
(e21)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e28)(C1-C6)烷氧基(C1-C6)烷基;
(e29)(C2-C6)炔氧基;
(e30)氰基;
(e31)(C2-C6)炔基;
(e32)(C1-C6)烷氧基羰基(C1-C6)烷基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基;
(e35)R1R2N羰基,此处R1和R2与上述相同;
(e36)R1R2N羰基(C1-C6)烷氧基,此处R1和R2与上述相同;或
(e37)R1R2N羰基卤代(C1-C6)烷氧基,此处R1和R2与上述相同,
X2可以与X3键合,与它们键合的碳原子一同形成5~8元的脂肪族环,该脂肪族环可具有选自(C1-C6)烷基和羰基中的1~5个取代基,●符号的部分与苯并咪唑键合。
[2]根据权利要求1所述的苯并咪唑化合物或其盐类,其中,
R表示:
(a1)(C1-C6)烷基;或,
(a4)卤代(C1-C6)烷基,
Y1、Y2、Y3和Y4可以相同或不同,并且表示:
(b1)氢原子;
(b2)卤素原子;
(b3)(C1-C6)烷基;或
(b4)卤代(C1-C6)烷基,
X1和X4可以相同或不同,并且表示:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X2表示:
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)(C1-C12)烷基;
(d5)(C3-C6)环烷基;
(d6)(C2-C12)烯基;
(d7)(C2-C12)炔基;
(d9)卤代(C1-C6)烷基;
(d11)(C1-C6)烷基硫基;
(d12)(C1-C6)烷基亚磺酰基;
(d13)(C1-C6)烷基磺酰基;
(d14)卤代(C1-C6)烷基硫基;
(d17)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d19)(C1-C6)烷基羰基;
(d20)(C1-C6)烷氧基羰基;
(d21)(C2-C6)炔氧基羰基;
(d22)(C1-C6)烷基硫基羰基;
(d23)(C1-C6)烷氧基羰基(C1-C6)烷基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d25)芳氧基(C1-C6)烷基;
(d26)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C1-C6)烷基;
(d27)芳氧基羰基;
(d28)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(d29)芳基羰基;
(d30)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基羰基;
(d31)芳基(C1-C6)烷基;
(d32)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d38)R1R2N羰基,此处R1和R2与上述相同;
(d39)R1R2N磺酰基,此处R1和R2与上述相同;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d44)(C3-C12)环烷基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d47)(C3-C6)环烷基(C1-C6)烷基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d51)(C1-C6)烷基羰氧基(C1-C6)烷基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基;
(d56)(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d57)卤代(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d58)芳基(C1-C6)烷基硫基;或
(d59)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基硫基,
X3表示:
(e1)氢原子;
(e2)卤素原子;
(e3)(C1-C6)烷基;
(e4)卤代(C1-C6)烷基;
(e5)(C1-C6)烷氧基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e8)(C1-C6)烷基硫基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e10)(C1-C6)烷氧基羰基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e14)芳基磺酰基;
(e15)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基磺酰基;
(e20)芳基(C1-C6)烷氧基;
(e21)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e28)(C1-C6)烷氧基(C1-C6)烷基;
(e29)(C2-C6)炔氧基;
(e30)氰基;
(e31)(C2-C6)炔基;
(e32)(C1-C6)烷氧基羰基(C1-C6)烷基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基;
(e35)R1R2N羰基,此处R1和R2与上述相同;
(e36)R1R2N羰基(C1-C6)烷氧基,此处R1和R2与上述相同;或
(e37)R1R2N羰基卤代(C1-C6)烷氧基,此处R1和R2与上述相同,
X2可以与X3键合,与它们键合的碳原子一同形成5~8元的脂肪族环,该脂肪族环可具有选自(C1-C6)烷基和羰基中的1~5个取代基。
[3]根据权利要求1或2所述的苯并咪唑化合物或其盐类,其中,
Q为Q-2、Q-3或Q-4。
[4]一种农艺和园艺用杀虫杀螨剂,其含有:
[1]~[3]中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
[5]一种农艺和园艺用杀虫杀螨剂的使用方法,其中,
用[1]~[3]中任一项所述的苯并咪唑化合物或其盐类的有效量对植物或土壤进行处理。
[6]一种用于动物的外部寄生虫防治剂,其含有:
[1]~[3]中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
[7]一种用于动物的内部寄生虫防治剂,其含有:
[1]~[3]中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
[发明的效果]
本发明的在2位键合含氮杂环基的氮原子,在1位具有特定的磺酰基的苯并咪唑化合物或其盐类,不仅具有作为农艺和园艺用杀虫杀螨剂的优异的效果,并且对寄生于犬、猫这样的宠物或牛、羊等家畜的害虫也具有效果。
[本发明的具体实施方式]
本发明的在2位键合含氮杂环基的氮原子并且在1位具有特定的磺酰基的苯并咪唑化合物或其盐类的通式(1)的定义中,“卤代”是指“卤素原子”,表示氟原子、氯原子、溴原子或碘原子。
“(C1-C6)烷基”例如表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、新戊基、2,3-二甲基丙基、1-乙基丙基、1-甲基丁基、2-甲基丁基、正己基、异己基、2-己基、3-己基、2-甲基戊基、3-甲基戊基、1,1,2-三甲基丙基、3,3-二甲基丁基等直链或支链状的碳原子数为1~6的烷基,“(C2-C6)烯基”例如表示乙烯基、烯丙基、异丙烯基、1-丁烯基、2-丁烯基、2-甲基-2-丙烯基、1-甲基-2-丙烯基、2-甲基-1-丙烯基、戊烯基、1-己烯基、3,3-二甲基-1-丁烯基等直链或分链状的碳原子数为2~6的烯基,“(C2-C6)炔基”例如表示乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、3-甲基-1-丙炔基、2-甲基-3-丙炔基、戊炔基、1-己炔基、3-甲基-1-丁炔基、3,3-二甲基-1-丁炔基等直链或分链状的碳原子数为2~6的炔基。
“(C1-C12)烷基”例如表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、新戊基、2,3-二甲基丙基、1-乙基丙基、1-甲基丁基、正己基、异己基、1,1,2-三甲基丙基、庚基、辛基、壬基、癸基、十一烷基、十二烷基等直链或支链状的碳原子数1~12个烷基,“(C2-C12)烯基”例如表示乙烯基、烯丙基、异丙烯基、1-丁烯基、2-丁烯基、2-甲基-2-丙烯基、1-甲基-2-丙烯基、2-甲基-1-丙烯基、戊烯基、1-己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一碳烯基、十二碳烯基等直链或分链状的碳原子数为2~12的烯基,“(C2-C12)炔基”例如表示乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、3-甲基-1-丙炔基、2-甲基-3-丙炔基、戊炔基、1-己炔基、庚炔基、辛炔基、壬炔基、癸炔基、十一炔基、十二炔基等直链或分链状的碳原子数为2~12的炔基。
“(C3-C6)环烷基”例如表示环丙基、环丁基、环戊基、环己基等碳原子数为3~6的环状烷基,作为“(C1-C6)烷氧基”,例如表示甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、叔戊氧基、新戊氧基、2,3-二甲基丙氧基、1-乙基丙氧基、1-甲基丁氧基、正己氧基、异己氧基、1,1,2-三甲基丙氧基等直链或支链状的碳原子数为1~6的烷氧基。
“(C3-C12)环烷基”例如表示环丙基、环丁基、环戊基、环己基、环戊基、环辛基、环壬基、环癸基等碳原子数为3~12的环状烷基、降冰片基、金刚烷基等桥环状烷基等。
作为“(C1-C6)烷硫基”,例如表示甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、仲丁硫基、叔丁硫基、正戊硫基、异戊硫基、叔戊硫基、新戊硫基、2,3-二甲基丙硫基、1-乙基丙硫基、1-甲基丁硫基、正己硫基、异己硫基、1,1,2-三甲基丙硫基等直链或支链状的碳原子数为1~6的烷硫基,作为“(C1-C6)烷基亚磺酰基”,例如表示甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、正戊基亚磺酰基、异戊基亚磺酰基、叔戊基亚磺酰基、新戊基亚磺酰基、2,3-二甲基丙基亚磺酰基、1-乙基丙基亚磺酰基、1-甲基丁基亚磺酰基、正己基亚磺酰基、异己基亚磺酰基、1,1,2-三甲基丙基亚磺酰基等直链或支链状的碳原子数为1~6的烷基亚磺酰基,作为“(C1-C6)烷基磺酰基”,例如表示甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正戊基磺酰基、异戊基磺酰基、叔戊基磺酰基、新戊基磺酰基、2,3-二甲基丙基磺酰基、1-乙基丙基磺酰基、1-甲基丁基磺酰基、正己基磺酰基、异己基磺酰基、1,1,2-三甲基丙基磺酰基等直链或支链状的碳原子数为1~6的烷基磺酰基。
“(C1-C6)烷基”、“(C2-C6)烯基”、“(C2-C6)炔基”、“(C3-C6)环烷基”、“(C1-C6)烷氧基”、“(C1-C6)烷硫基”、“(C1-C6)烷基亚磺酰基”或“(C1-C6)烷基磺酰基”的可取代的位置任选取代有一个或两个以上的卤素原子,在取代的卤素原子为两个以上的情况下,卤素原子可以相同或不同。分别表示为“卤代(C1-C6)烷基”、“卤代(C2-C6)烯基”、“卤代(C2-C6)炔基”、“卤代(C3-C6)环烷基”、“卤代(C1-C6)烷氧基”、“卤代(C1-C6)烷硫基”、“卤代(C1-C6)烷基亚磺酰基”或“卤代(C1-C6)烷基磺酰基”。
“(C1-C6)”、“(C2-C6)”、“(C3-C6)”、“(C1-C12)”等的表达,表示各种取代基的碳原子数的范围。并且,即使对于与所述取代基连接的基团也可表示所述定义,例如,“(C3-C6)环烷基(C1-C6)烷基”的情况表示直链或支链状的碳原子数为3~6的环烷基与直链或支链状的碳原子数为1~6的烷基键合。
“芳基”例如表示苯基、1-萘基、2-萘基等碳原子数为6~10的芳香族烃基。
“杂芳基”例如表示呋喃基、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(Oxadiazolyl)、噻二唑基(Thiadiazolyl)、三唑基、四唑基、三嗪基等具有1~4个选自氮原子、氧原子、硫原子(硫原子可被氧化)等中的杂原子的5或6元的芳香族杂环基。
“5~8元的脂肪族环”例如表示环戊烯、环己烯、环庚烯、环辛烯等碳原子数为5~8的环烯烃。
“(C1-C6)烷基羰基”例如表示乙酰基、丙酰基、丁酰基、异丁酰基、正丁基羰基、异丁基羰基、仲丁基羰基、叔丁基羰基、正戊基羰基、异戊基羰基、叔戊基羰基、新戊基羰基、2,3-二甲基丙基羰基、1-乙基丙基羰基、1-甲基丁基羰基、2-甲基丁基羰基、正己基羰基、异己基羰基、2-己基羰基、3-己基羰基、2-甲基戊基羰基、3-甲基戊基羰基、1,1,2-三甲基丙基羰基、3,3-二甲基丁基羰基等直链或支链状的碳原子数为1~6的烷基和羰基构成的烷基羰基。
作为“(C1-C6)烷氧基羰基”,例如表示甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、仲丁氧基羰基、叔丁氧基羰基、正戊氧基羰基、异戊氧基羰基、叔戊氧基羰基、新戊氧基羰基、2,3-二甲基丙氧基羰基、1-乙基丙氧基羰基、1-甲基丁氧基羰基、正己氧基羰基、异己氧基羰基、1,1,2-三甲基丙氧基羰基等直链或支链状的碳原子数为1~6的烷氧基和羰基构成的烷氧基羰基。
作为本发明的通式(1)表示的苯并咪唑化合物的盐类,例如可举出:盐酸盐、硫酸盐、硝酸盐、磷酸盐等无机酸盐类;乙酸盐、富马酸盐、马来酸盐、草酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐等有机酸盐类;钠离子、钾离子、钙离子、三甲基铵等与无机碱或有机碱形成的盐类。
本发明的通式(1)表示的苯并咪唑化合物及其盐,在其结构式中具有一个或多个不对称中心时,有存在2种以上的光学异构体和非对映异构体的情况,本发明全部包含各个光学异构体和以任意的比例包含它们的混合物。此外,本发明的通式(1)表示的苯并咪唑化合物及其盐,存在在其结构式中存在源自碳-碳双键的2种几何异构体的情况,本发明全部包含各个几何异构体和以任意的比例包含它们的混合物。
本发明的通式(1)表示的苯并咪唑化合物或其盐类中,
作为R,优选为(a1)(C1-C6)烷基;或(a4)卤代(C1-C6)烷基。
作为Y1、Y2、Y3和Y4,优选可以相同或不同,为(b1)氢原子;(b2)卤素原子;(b3)(C1-C6)烷基;或(b4)卤代(C1-C6)烷基。
作为X1和X4,优选可以相同或不同,为(c1)氢原子;或(c2)(C1-C6)烷基。
作为X2,优选为:
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)(C1-C12)烷基;
(d5)(C3-C6)环烷基;
(d6)(C2-C12)烯基;
(d7)(C2-C12)炔基;
(d9)卤代(C1-C6)烷基;
(d11)(C1-C6)烷基硫基;
(d12)(C1-C6)烷基亚磺酰基;
(d13)(C1-C6)烷基磺酰基;
(d14)卤代(C1-C6)烷基硫基;
(d17)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d19)(C1-C6)烷基羰基;
(d20)(C1-C6)烷氧基羰基;
(d21)(C2-C6)炔氧基羰基;
(d22)(C1-C6)烷基硫基羰基;
(d23)(C1-C6)烷氧基羰基(C1-C6)烷基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d25)芳氧基(C1-C6)烷基;
(d26)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C1-C6)烷基;
(d27)芳氧基羰基;
(d28)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(d29)芳基羰基;
(d30)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基羰基;
(d31)芳基(C1-C6)烷基;
(d32)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d38)R1R2N羰基,此处R1和R2与上述相同;
(d39)R1R2N磺酰基,此处R1和R2与上述相同;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d44)(C3-C12)环烷基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d47)(C3-C6)环烷基(C1-C6)烷基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d51)(C1-C6)烷基羰氧基(C1-C6)烷基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基;
(d56)(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d57)卤代(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d58)芳基(C1-C6)烷基硫基;或
(d59)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基硫基。
作为X3,优选为:
(e1)氢原子;
(e2)卤素原子;
(e3)(C1-C6)烷基;
(e4)卤代(C1-C6)烷基;
(e5)(C1-C6)烷氧基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e8)(C1-C6)烷基硫基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e10)(C1-C6)烷氧基羰基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e14)芳基磺酰基;
(e15)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基磺酰基;
(e20)芳基(C1-C6)烷氧基;
(e21)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e28)(C1-C6)烷氧基(C1-C6)烷基;
(e29)(C2-C6)炔氧基;
(e30)氰基;
(e31)(C2-C6)炔基;
(e32)(C1-C6)烷氧基羰基(C1-C6)烷基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基;
(e35)R1R2N羰基,此处R1和R2与上述相同;
(e36)R1R2N羰基(C1-C6)烷氧基,此处R1和R2与上述相同;或
(e37)R1R2N羰基卤代(C1-C6)烷氧基,此处R1和R2与上述相同;
X2可以与X3键合,与它们键合的碳原子一同形成5~8元的脂肪族环,该脂肪族环可具有选自(C1-C6)烷基和羰基中的1~5个取代基。
作为Q,进一步优选为Q-2、Q-3或Q-4。
作为R,进一步优选为(a1)(C1-C6)烷基。
作为Y1、Y2、Y3和Y4,进一步优选可以相同或不同,为(b1)氢原子;或(b2)卤素原子。
作为X1和X4,进一步优选为(c1)氢原子。
作为X2,进一步优选为
(d7)(C2-C12)炔基;
(d9)卤代(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d20)(C1-C6)烷氧基羰基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;或
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基。
作为X3,进一步优选为:
(e2)卤素原子;
(e4)卤代(C1-C6)烷基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e29)(C2-C6)炔氧基;
(e31)(C2-C6)炔基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;或
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基。
本发明的通式(1)表示的苯并咪唑化合物或其盐类例如可通过下述制造方法来制造,但是本发明不限于此。
制造方法1
[化学式3]
Q和R与所述相同,L表示卤素原子,PG表示SEM等保护基,Y1-4表示Y1、Y2、Y3和Y4。
工序[A]的制造方法
通式(1-1)表示的苯并咪唑化合物可通过用通式(1-2)表示的化合物和通式(2)表示的含氮杂环化合物根据J.O.C.,2011,76,8262-8269中记载的方法进行制造。
反应结束后,可通过常规方法从包含目标产物的反应体系中分离目标产物,可根据需要通过重结晶、柱层析等进行纯化而制造目标产物。此外,可在未将通式(1-1)表示的苯并咪唑化合物从反应体系中分离的情况下,进行接下来的工序。
工序[B]的制造方法
通式(1)表示的苯并咪唑化合物可通过下述方式制造:将通式(1-1)表示的苯并咪唑化合物和通式(3)表示的化合物在碱和不活泼溶剂的存在下进行反应。
作为本反应中使用的碱,例如可举出:氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、氢化钠、氢化钾等无机碱类、乙酸钠、乙酸钾等乙酸盐类、叔丁醇钾、甲醇钠、乙醇钠等碱金属烷氧化物类;三乙胺、二异丙基乙胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)等叔胺类、吡啶、二甲基氨基吡啶(DMAP)等含氮芳香族化合物等,其使用量在相对于通式(1-1)表示的化合物通常为1倍摩尔~10倍摩尔的范围内使用。
作为本反应中使用的不活泼溶剂,只要不会显著阻碍本反应的进行即可,例如可举出:苯、甲苯、二甲苯等芳香族烃类、氯苯、二氯苯等卤化芳香族烃类、乙醚、甲基叔丁基醚、二噁烷、四氢呋喃(THF)等链状或环状醚类、二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮(NMP)等酰胺类、丙酮、甲基乙基酮等酮类、二甲基亚砜(DMSO)、1,3-二甲基-2-咪唑烷酮(DMI)等极性溶剂、甲醇、乙醇、丙醇、异丙醇等醇类等不活泼溶剂,这些不活泼溶剂可以单独使用或混合使用2种以上。
由于该反应是等摩尔反应,因此等摩尔使用各反应剂即可,但是也可过量使用任意反应剂。可在反应温度为室温至使用的不活泼溶剂的沸点范围内进行,反应时间取决于反应规模、反应温度而不是恒定的,在几分钟~48小时的范围内进行即可。
在反应结束后,通过常规方法从包含目标产物的反应体系中分离出目标产物即可,可根据需要通过重结晶、柱层析等进行纯化来制造本申请发明的化合物。
工序[C]的制造方法
在无法通过工序[A]的制造方法进行制造的情况下,可通过经由通式(1-3)表示的苯并咪唑化合物的途径进行制造。通式(1-3)表示的苯并咪唑化合物可通过下述方式制造:将通式(1-2)表示的苯并咪唑化合物和三氯氧磷、溴氧磷或亚硫酰氯等卤化剂在不活泼溶剂的存在下或不存在下进行反应。
作为本反应中使用的不活泼溶剂,是不显著抑制本反应的进行的即可,例如可举出:苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤代烃类;氯苯、二氯苯等卤化芳香族烃类等不活泼溶剂,这些不活泼溶剂可以单独使用或混合使用2种以上。
由于该反应是等摩尔反应,因此等摩尔使用各反应剂即可,但是如上所述,不使用溶剂时可过量使用卤化剂。可在反应温度为室温至使用的不活泼溶剂的沸点范围内进行,反应时间取决于反应规模、反应温度而不是恒定的,在几分钟~48小时的范围内进行即可。
在反应结束后,通过常规方法从包含目标产物的反应体系中分离出目标产物即可,可根据需要通过重结晶、柱层析等进行纯化来制造目标产物。
工序[D]的制造方法
通式(1-4)表示的苯并咪唑化合物可通过下述方式制造:将通式(1-3)表示的苯并咪唑化合物和甲氧基甲基氯(MOMCl)、甲氧基乙氧基甲基氯(MEMCl)、2-(三甲基甲硅烷基)乙氧基甲基氯(SEMCl)等保护剂在碱和不活泼溶剂的存在下进行反应。
作为本反应中使用的碱,例如可举出:氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、氢化钠、氢化钾等无机碱类、乙酸钠、乙酸钾等乙酸盐类、叔丁醇钾、甲醇钠、乙醇钠等碱金属烷氧化物类;三乙胺、二异丙基乙胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)等叔胺类、吡啶、二甲基氨基吡啶(DMAP)等含氮芳香族化合物等,其使用量在相对于通式(1-3)表示的化合物通常为1倍摩尔~10倍摩尔的范围内使用。
作为本反应中使用的不活泼溶剂,只要不会显著阻碍本反应的进行即可,例如可举出:苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤代烃类;氯苯、二氯苯等卤化芳香族烃类、乙醚、甲基叔丁基醚、二噁烷、四氢呋喃(THF)等链状或环状醚类、乙酸乙酯等酯类、二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮(NMP)等酰胺类、丙酮、甲基乙基酮等酮类、二甲基亚砜(DMSO)、1,3-二甲基-2-咪唑烷酮(DMI)等极性溶剂、吡啶等含氮芳香族化合物等不活泼溶剂,这些不活泼溶剂可以单独使用或混合使用2种以上。
由于该反应是等摩尔反应,因此等摩尔使用各反应剂即可,但是也可过量使用任意反应剂。可在反应温度为室温至使用的不活泼溶剂的沸点范围内进行,反应时间取决于反应规模、反应温度而不是恒定的,在几分钟~48小时的范围内进行即可。
在反应结束后,通过常规方法从包含目标产物的反应体系中分离出目标产物即可,可根据需要通过重结晶、柱层析等进行纯化来制造目标产物。此外,可以在不从反应体系中分离中间体的情况下进行接下来的工序。
工序[E]的制造方法
通式(1-5)表示的苯并咪唑化合物可通过下述方式制造:将通式(1-4)表示的苯并咪唑化合物和通式(2)表示的含氮杂环化合物在不活泼溶剂和碱存在下进行反应。
作为本反应中使用的碱,例如可举出:氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、氢化钠等无机碱类、乙酸钠、乙酸钾等乙酸盐类、叔丁醇钾、甲醇钠、乙醇钠等碱金属烷氧化物类;三乙胺、二异丙基乙胺、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)等叔胺类、吡啶、二甲基氨基吡啶(DMAP)等含氮芳香族化合物等,其使用量在相对于通式(1-4)表示的化合物通常为1倍摩尔~10倍摩尔的范围内使用。
作为本反应中使用的不活泼溶剂,只要不会显著阻碍本反应的进行即可,例如可举出:苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤代烃类、氯苯、二氯苯等卤化芳香族烃类等、乙醚、四氢呋喃(THF)、二噁烷等链状或环状醚类、二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮(NMP)等酰胺类,这些不活泼溶剂可以单独使用或混合使用2种以上。
由于该反应是等摩尔反应,因此等摩尔使用各反应剂即可,但是也可过量使用任意反应剂。可在反应温度为室温至使用的不活泼溶剂的沸点范围内进行,反应时间取决于反应规模、反应温度而不是恒定的,在几分钟~48小时的范围内进行即可。
在反应结束后,通过常规方法从包含目标产物的反应体系中分离出目标产物即可,可根据需要通过重结晶、柱层析等进行纯化来制造目标产物。此外,可在未将中间体从反应体系中分离的情况下,进行接下来的工序。
工序[F]的制造方法
通式(1-1)表示的苯并咪唑化合物,可通过将通式(1-5)表示的苯并咪唑化合物根据Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS(4th Edition)561-565等中记载的方法来对保护基进行脱保护。
在反应结束后,通过常规方法从包含目标产物的反应体系中分离出目标产物即可,可根据需要通过重结晶、柱层析等进行纯化来制造目标产物。此外,可以在不从反应体系中分离中间体的情况下进行工序[B]。
制造方法2
[化学式4]
X1和X4与所述相同,PG表示SEM等保护基,Y1-4表示Y1、Y2、Y3和Y4,Ar表示无取代芳基或取代芳基。
在制造方法1公开的制造方法以外,也可通过上述方法进行制造。通式(1-52)表示的苯并咪唑化合物可通过下述方式制造:将根据制造方法1公开的方法而制造得到的通式(1-51)表示的化合物,在甲醇、乙醇、丙醇、异丙醇、四氢呋喃等溶剂中,与硼氢化钠、氢化硼钾等还原剂反应。
通式(1-53)表示的化合物可通过将通式(1-52)表示的化合物和酚类根据被称为所谓的光延反应的文献记载的(Bull.Chem.Soc.Jpn.1967,40,935)方法来制造。
通式(1-11)表示的化合物可通过制造方法1记载的工序F来制造,可进一步通过工序B而诱导为本申请发明化合物。
所述制造方法中使用的含氮杂环化合物可原样使用市售的,也可通过下述方法制造并使用。
含氮杂环化合物的制造方法1
[化学式5]
Hal表示卤素原子,X21表示烷基、芳基或取代芳基。
通式(QH-21)表示的化合物可通过下述方式制造:将市售的咪唑在乙腈、丙腈等溶剂存在下,与NCS(N-氯代琥珀酰亚胺)、NBS(N-溴代琥珀酰亚胺)、DBH(1,3-二溴-5,5-二甲基乙内酰脲)、DIH(1,3-二碘-5,5-二甲基乙内酰脲)等卤化剂反应。
通式(QH-22)表示的化合物可通过将通式(QH-21)表示的化合物和乙炔化合物通过被称为所谓的薗头反应的文献记载的(Tetrahedron Lett..1975,50,4467,Synthesis,364-365(1981),Organic Letters,11(1),221-224、2009)方法来制造。
通式(QH-23)表示的化合物可通过将通式(QH-22)表示的乙炔化合物通过接触还原反应进行制造。接触还原反应,可通过在催化剂存在下、常压下或者加压下、不活泼溶剂的存在下或者非存在下、氢氛围下进行反应。
通式(QH-24)表示的化合物可通过日本特开2001-122836号公开的方法来制造。
含氮杂环化合物的制造方法2
[化学式6]
X1和X3与所述相同,R1表示C1~C6的烷基。
通式(QH-25)表示的化合物可通过将根据文献记载的方法(WO2013/063221号小册子)制造的1H-吡唑-4-羧酸根据Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS(4th Edition)582-588所述的方法诱导为酯化合物。
含氮杂环化合物的制造方法3
[化学式7]
X1和X3与所述相同,Hal表示卤素原子。
通式(QH-26)表示的化合物可通过与所述含氮杂环化合物的制造方法1的QH-21相同的制造方法来制造。
含氮杂环化合物的制造方法4
[化学式8]
PG表示保护基,X23表示C1-C6的卤代烷基,L表示卤素原子或三氟甲磺酸酯等离去基团。
通式(QH-27)表示的化合物,可将由市售的乙氧基亚甲基丙二酸二乙酯和水合肼制造得到的1H-吡唑-3-羟基-4-羧酸乙酯通过Greene's PROTECTIVE GROUPS in ORGANICSYNTHESIS(4th Edition)582-588所述的方法保护吡唑环1位。将该吡唑环1位被保护了的化合物和X23L在二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)等溶剂中,用碳酸钠或碳酸钾进行反应后,通过Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS(4th Edition)582-588所述的方法对吡唑环的保护基进行脱保护来制造。
接下来,在下文中表示本发明化合物及其制造中间体的具体例。下述表中,Me表示甲基,Et表示乙基,n-Pr表示正丙基,i-Pr表示异丙基,n-Bu表示正丁基,i-Bu表示异丁基,t-Bu表示叔丁基,n-Pen表示正戊基,t-Amyl表示叔戊基,Ph表示苯基,c-Pr表示环丙基。E、Z表示几何异构体。物理性质表示熔点(℃)、折射率nD(测定温度;℃)或H1-NMR,H1-NMR数据示于第16表~第24表、第39表~第44表。
[化学式9]
[表1]
第1表
式中,X1和X4表示氢原子。
[表2]
第2表
式中,X1和X4表示氢原子。
[表3]
第3表
式中,X1和X4表示氢原子。
[化学式10]
[表4]
第4表
[表5]
第5表
[表6]
第6表
[表7]
第7表
[表8]
第8表
[表9]
第9表
[表10]
第10表
[化学式11]
[表11]
第11表
[化学式12]
[表12]
第12表
[化学式13]
[表13]
第13表
[化学式14]
[表14]
第14表
[化学式15]
[表15]
第15表
[表16]
第16表
[表17]
第17表
[表18]
第18表
[表19]
第19表
[表20]
第20表
[表21]
第21表
[表22]
第22表
[表23]
第23表
[表24]
第24表
[化学式16]
[表25]
第25表
[表26]
第26表
[化学式17]
[表27]
第27表
[表28]
第28表
[表29]
第29表
[表30]
第30表
[表31]
第31表
[表32]
第32表
[表33]
第33表
[化学式18]
[表34]
第34表
[化学式19]
[表35]
第35表
[化学式20]
[表36]
第36表
[化学式21]
[表37]
第37表
[化学式22]
[表38]
第38表
[表39]
第39表
[表40]
第40表
[表41]
第41表
[表42]
第42表
[表43]
第43表
[表44]
第44表
含有本发明的通式(1)表示的苯并咪唑化合物或其盐类作为有效成分的用于农业园艺的杀虫杀螨剂适用于防治各种危害水稻、果树、蔬菜、其它作物和花卉类的农林、园艺、储粮害虫、卫生害虫或线虫类等害虫、螨类。
作为所述害虫或线虫类等,例举如下。
作为鳞翅目(Lepidoptera)害虫,例如可举出:褐边绿刺蛾(Parasa consocia)、桥夜蛾(Anomis mesogona)、柑橘凤蝶(Papilio xuthus)、日豆小卷蛾(Matsumuraesesazukivora)、麻田豆秆野螟(Ostrinia scapulalis)、非洲粘虫(Spodoptera exempta)、美国白蛾(Hyphantria cunea)、亚洲玉米螟(Ostrinia furnacalis)、东方粘虫(Pseudaletiaseparata)、Tinea translucens、尖翅小卷蛾(Bactra furfuryla)、稻苞虫(Parnaraguttata)、稻显纹刷须野螟(Marasmia exigua)、稻苞虫(Parnara guttata)、水稻大螟(Sesamia inferens)、甘薯麦蛾(Brachmia triannulella)、黄刺蛾(Monema flavescens)、粉纹夜蛾(Trichoplusia ni)、Pleuroptya ruralis、小蜻蜓尺蛾(Cystidia couaggaria)、亮灰蝶(Lampides boeticus)、咖啡透翅天蛾(Cephonodes hylas)、棉铃虫(Helicoverpaarmigera)、曼蚕舟蛾(Phalerodonta manleyi)、大避债蛾(Eumeta japonica)、欧洲粉蝶(Pieris brassicae)、天幕毛虫(Malacosoma neustria testacea)、柿举肢蛾(Stathmopoda masinissa)、柿细蛾(Cuphodes diospyrosella)、梣黄卷蛾(Archipsxylosteanus)、黄地老虎(Agrotis segetum)、甘蔗黄螟(Tetramoera schistaceana)、黄凤蝶(Papilio machaon hippocrates)、黄斑蝙幅蛾(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(Lobesiabotrana)、中国绿剌蛾(Latoia sinica)、皮暗斑螟(Euzophera batangensis)、慈姑褐纹卷蛾(Phalonidia mesotypa)、桑斑灯蛾(Spilosoma imparilis)、桑绢野螟(Glyphodespyloalis)、桑新小卷蛾(Olethreutes mori)、幕谷蛾(Tineola bisselliella)、编幅蛾(Endoclyta excrescens)、谷蛾(Nemapogon granellus)、苹果透翅蛾(Synanthedonhector)、苹果蠹蛾(Cydia pomonella)、小菜蛾(Plutella xylostella)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、Sesamia calamistis、三化螟(Scirpophaga incertulas)、蓝草螟蛾(Pediasia teterrellus)、马铃薯块茎蛾(Phthorimaea operculella)、苹蚁舟蛾(Stauropusfagi persimilis)、豆荚螟(Etiella zinckenella)、甜菜夜蛾(Spodopteraexigua)、白斑蝙幅蛾(Palpifer sexnotata)、灰翅夜蛾(Spodoptera mauritia)、稻白螟(Scirpophaga innotata)、八字地老虎(Xestia c-nigrum)、淡剑贪夜蛾(Spodopteradepravata)、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)、松村氏卷蛾(Matsumuraeses falcana)、烟夜蛾(Helicoverpa assulta)、黑点丫纹夜蛾(Autographanigrisigna)、小地老虎(Agrotis ipsilon)、茶毒蛾(Euproctis pseudoconspersa)、棉褐带卷蛾(Adoxophyes orana)、茶细蛾(Caloptilia theivora)、茶长卷蛾(Homonamagnanima)、烟草粉斑螟(Ephestia elutella)、茶蓑蛾(Eumeta minuscula)、杨扇舟蛾(Clostera anachoreta)、苇实夜蛾(Heliothis maritima)、葡萄长须卷蛾(Sparganothispilleriana)、玉米茎夜蛾(Busseola fusca)、东方毒蛾(Euproctis subflava)、褐纹大尺蛾(Biston robustum)、美洲棉铃虫(Heliothis zea)、白斑烦夜蛾(Aedia leucomelas)、梨娜刺蛾(Narosoideus flavidorsalis)、梨剑纹夜蛾(Viminia rumicis)、Bucculatrixpyrivorella、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)、纵带球须刺蛾(Scopelodescontractus)、旋古毒蛾(Orgyia thyellina)、草地夜蛾(Spodoptera frugiperda)、Ostrinia zaguliaevi、双带夜蛾(Naranga aenescens)、茶蚕蛾(Andraca bipunctata)、葡萄透翅蛾(Paranthrene regalis)、缺角天蛾(Acosmeryx castanea)、葡萄潜叶蛾(Phyllocnistis toparcha)、葡萄小食心虫(Endopiza viteana)、环针单纹卷蛾(Eupoecillia ambiguella)、大豆夜蛾(Anticarsia gemmatalis)、烟草云卷蛾(Cnephasiacinereipalpana)、舞毒蛾(Lymantria dispar)、赤松毛虫(Dendrolimus spectabilis)、大豆食心虫(Leguminivora glycinivorella)、豆荚野螟(Maruca testulalis)、豆小卷蛾(Matsumuraeses phaseoli)、大豆花细蛾(Caloptilia soyella)、柑橘潜叶蛾(Phyllocnistis citrella)、豆啮叶野螟(Omiodes indicate)、杏黄卷蛾(Archipsfuscocupreanus)、银纹夜蛾(Acanthoplusia agnata)、黑艳避债蛾(Bambalina sp.)、桃蛀果蛾(Carposina niponensis)、桃蛀螟(Conogethes punctiferalis)、榆透翅蛾(Synanthedon sp.)、桃潜蛾(Lyonetia clerkella)、玉斑凤蝶(Papilio helenus)、斑缘豆粉蝶(Colias erate poliographus)、苹掌舟蛾(Phalera flavescens)、日本纹白蝶(Pieris rapae crucivora)、菜粉蝶(Pieris rapae)等粉蝶类、桑毛虫(Euproctissimilis)、铃木凤眼蜂(Acrolepiopsis suzukiella)、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)、Odonestis prunijaponensis、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(Spilonotalechriaspis)、梨星毛虫(Illiberis pruni)、Argyresthia conjugella、猛花细蛾(Caloptilia zachrysa)、梨黄卷蛾(Archips breviplicanus)、小造桥夜蛾(Anomisflava)、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)和鼎点钻夜蛾(Eariascupreoviridis)等。
作为半翅目(Hemiptera)害虫,例如可举出:黑须稻绿蝽(Nezara antennata)、赤条纤盲蝽(Stenotus rubrovittatus)、赤条蝽(Graphosoma rubrolineatum)、条赤须盲蝽(Trigonotylus coelestialium)等、黄伊缘蝽(Aeschynteles maculatus)、Creontiadespallidifer、棉二点红蝽(Dysdercus cingulatus)、褐圆介壳虫(Chrysomphalus ficus)、红圆蚧(Aonidiella aurantii)、油蝉(Graptopsaltria nigrofuscata)、麦长蝽(Blissusleucopterus)、吹绵蚧壳虫(Icerya purchasi)、壁蝽(Piezodorus hybneri)、稻蝽象(Lagynotomus elongatus)、白翅叶蝉(Thaia subrufa)、稻黑蝽(Scotinopharalurida)、玫瑰蚜(Sitobion ibarae)、Stariodes iwasakii、椰圆盾蚧(Aspidiotusdestructor)、淡色泰盲蝽(Taylorilygus pallidulus)、杏瘤蚜(Myzusmu mecola)、梅白蚧(Pseudaulacaspis prunicola)、豌豆蚜(Acyrthosiphon pisum)、纹须同缘椿象(Anacanthocoris striicornis)、跃盲蝽(Ectometopterus micantulus)、日本二星蝽(Eysarcoris lewisi)、巨叶足虫(Molipteryx fuliginosa)、大青叶蝉(Cicadellaviridis)、红腹缢管蚜(Rhopalosophum rufiabdominalis)、橄榄黑盔蚧(Saissetiaoleate)、温室粉虱(Trialeurodes vaporariorum)、Aguriahana quercus、草盲蝽属(Lygusspp.)、桦绵斑蚜(Euceraphis punctipennis)、柑橘介壳虫(Andaspis kashicola)、橘软蜡蚧(Coccus pseudomagnoliarum)、甘蔗长蝽(Cavelerius saccharivorus)、菊贝脊网蝽(Galeatus spinifrons)、光褐菊蚜(Macrosiphoniella sanborni)、黄圆蹄盾蚧(Aonidiella citrina)、茶翅蝽(Halyomorpha mista)、冠网蝽(Stephanitisfasciicarina)、樟个木虱(Trioza camphorae)、中稻缘蝽(Leptocorisa chinensis)、Trioza quercicola、褐角肩网蝽(Uhlerites latius)、葡萄斑叶蝉(Erythroneuracomes)、Paromius exiguus、柘柳重圆盾蚧(Duplaspidiotus claviger)、二条斑黑尾叶蝉(Nephotettix nigropictus)、Halticiellus insularis、甘蔗扁角飞虱(Perkinsiellasaccharicida)、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)、Togo hemipterus、橘二叉蚜(Toxoptera aurantii)、Saccharicoccus sacchari、蔗根蚜(Geoica lucifuga)、瓶额飞虱(Numata muiri)、圣琼斯康盾蚧(Comstockaspis perniciosa)、矢尖蚧(Unaspis citri)、茄无网长管蚜(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(Aspidiotushederae)、粟缘蝽(Liorhyssus hyalinus)、Calophya nigridorsalis、白背飞虱(Sogatella furcifera)、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、烟盲蝽(Cyrtopeltis tennuis)、烟粉虱(Bemisiatabaci)、桃蜡蚧(Lecanium persicae)、Parlatoria theae、牡丹网盾蚧(Pseudaonidiapaeoniae)、茶小绿叶蝉(Empoasca onukii)、小珀椿象(Plautia stali)、百合西圆尾蚜(Dysaphis tulipae)、马铃薯长管蚜(Macrosiphum euphorbiae)、杜鹃军配虫(Stephanitis pyrioides)、角蜡蚧(Ceroplastes ceriferus)、Parlatoria camelliae、斯氏后丽盲蝽(Apolygus spinolai)、黑尾叶蝉(Nephotettix cincticeps)、青蝽(Glauciassubpunctatus)、杂毛合垫盲蝽(Orthotylus flavosparsus)、玉米蚜(Rhopalosiphummaidis)、玉米蜡蝉(Peregrinus maidis)、尖角二星蝽(Eysarcoris parvus)、温带臭虫(Cimex lectularius)、冷杉木虱(Psylla abieti)、褐飞虱(Nilaparvata lugens)、Psyllatobirae、Eurydema rugosum、梨二叉蚜(Schizaphis piricola)、Psylla pyricola、梨星片盾蚧(Parlatoreopsis pyri)、梨冠网蝽(Stephanitis nashi)、紫藤灰粉蚧(Dysmicoccuswistariae)、Lepholeucaspis japonica、梨扎圆尾蚜(Sappaphis piri)、萝卜蚜(Lipaphiserysimi)、中国台湾韭蚜、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)、Speusotettix subfusculus、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)、褐色肩网蝽(Uhlerites debile)、灰飞虱(Laodelphaxstriatella)、六斑菜蝽(Eurydema pulchrum)、长肩棘缘蝽(Cletus trigonus)、Cloviapunctata、Empoasca sp.、米兰褐软蚧(Coccus hesperidum)、莎草鼓胸长蝽(Pachybrachius luridus)、日本臀纹粉蚧(Planococcus kraunhiae)、Stenotusbinotatus、葡萄阿小叶蝉(Arboridia apicalis)、Macrosteles fascifrons、Dolycorisbaccarum、三环苜蓿盲蝽(Adelphocoris triannulatus)、葡萄根瘤蚜(Viteusvitifolii)、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(Riptortusclavatus)、Paratrioza cockerelli、柳尖胸沫蝉(Aphrophora costalis)、Lygusdisponsi、东亚草盲蝽(Lygus saundersi)、松白粉蚧(Crisicoccus pini)、松小叶蝉(Empoasca abietis)、Crisicoccus matsumotoi、豆蚜(Aphis craccivora)、臭蝽(Megacopta punctatissimum)、圆白星椿象(Eysarcoris guttiger)、Lepidosaphesbeckii、柑橘木虱(Diaphorina citri)、Toxoptera citricidus、桔臀纹粉蚧(Planococcuscitri)、柑桔裸粉虱(Dialeurodes citri)、茶树黑刺粉虱(Aleurocanthus spiniferus)、柑橘小粉蚧(Pseudococcus citriculus)、Zyginella citri、桔绵蜡蚧(Pulvinariacitricola)、柑桔介壳虫(Coccus discrepans)、茶树蛇眼蚧(Pseudaonidia duplex)、柑橘绵蚧(Pulvinaria aurantii)、Lecanium corni、稻绿蝽(Nezara viridula)、剌狭盲蝽(Stenodema calcaratum)、禾谷缢管蚜(Rhopalosiphum padi)、Sitobion akebiae、麦二叉蚜(Schizaphis graminum)、Sorhoanus tritici、李圆尾蚜(Brachycaudus helichrysi)、紫翅果蝽(Carpocoris purpureipennis)、桃蚜(Myzus persicae)、桃大尾蚜(Hyalopteruspruni)、柳蚜(Aphis farinose yanagicola)、杨柳网蝽(Metasalis populi)、矢尖蚧(Unaspis yanonensis)、黄槿木虱(Mesohomotoma camphorae)、Aphis spiraecola、苹果黄蚜(Aphis pomi)、榆蛎盾蚧(Lepidosaphes ulmi)、苹木虱(Psylla mali)、Heterocordylusflavipes、苹果瘤蚜(Myzus malisuctus)、Aphidonuguis mali、Orientus ishidai、Ovatusmalicolens、苹果绵蚜(Eriosoma lanigerum)、红蜡蚧(Ceroplastes rubens)和棉蚜(Aphis gossypii)等。
作为鞘翅目(Coleoptera)害虫,例如可举出:合欢双条天牛(Xystroceraglobosa)、青翅蚁形隐翅虫(Paederus fuscipes)、金边青花金龟(Eucetonia roelofsi)、绿豆象(Callosobruchus chinensis)、甘薯小象虫(Cylas formicarius)、苜蓿叶象甲(Hypera postica)、稻鳞象甲(Echinocnemus squameus)、水稻负泥虫(Oulema oryzae)、水稻负泥虫(Oulema oryzae)、荷花叶甲(Donacia provosti)、稻水象甲(Lissorhoptrusoryzophilus)、甘薯叶甲(Colasposoma dauricum)、西印度甘薯象甲(Euscepespostfasciatus)、墨西哥豆瓢虫(Epilachna varivestis)、菜豆象(Acanthoscelidesobtectus)、玉米根萤叶甲(Diabrotica virgifera virgifera)、李虎象(Involvuluscupreus)、黄守瓜(Aulacophora femoralis)、豌豆象(Bruchus pisorum)、马铃薯瓢虫(Epilachna vigintioctomaculata)、脊胸露尾甲(Carpophilus dimidiatus)、甜菜大龟甲(Cassida nebulosa)、粗背寡毛跳甲(Luperomorpha tunebrosa)、黄曲条菜跳甲(Phyllotreta striolata)、桑树黄星天牛(Psacothea hilaris)、黄斑天牛(Aeolestheschrysothrix)、Curculio sikkimensis、酱曲露尾甲(Carpophilus hemipterus)、小青花金龟(Oxycetonia jucunda)、根萤叶甲类(Diabrotica spp.)、墨绿彩丽金龟(Mimelasplendens)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium castaneum)、米象(Sitophilus oryzae)、亚扁粉盗(Palorus subdepressus)、Melolontha japonica、星天牛(Anoplophora malasiaca)、大点拟粉虫(Neatus picipes)、马铃薯甲虫(Leptinotarsadecemlineata)、十一星叶甲食根亚种(Diabrotica undecimpunctata howardi)、结缕草象甲(Sphenophorus venatus)、十四点负泥虫(Crioceris quatuordecimpunctata)、梅球颈象(Conotrachelus nenuphar)、Ceuthorhynchidius albosuturalis、小猿叶虫(Phaedonbrassicae)、烟草甲(Lasioderma serricorne)、Sitona japonicus、葡萄丽金龟(Adoretustenuimaculatus)、黄粉虫(Tenebrio molitor)、Basilepta balyi、Hypera nigrirostris、甜菜跳甲(Chaetocnema concinna)、古铜异丽金龟(Anomala cuprea)、Heptophyllapicea、茄二十八星瓢虫(Epilachna vigintioctopunctata)、长角叶甲(Diabroticalongicornis)、Eucetonia pilifera、叩甲类(Agriotes spp.)、黑毛皮蠹(Attagenusunicolor japonicus)、斑鞘豆叶甲(Pagria signata)、红铜丽金龟(Anomalarufocuprea)、姬帕谷甲(Palorus ratzeburgii)、褐菌虫(Alphitobius laevigatus)、小圆皮蠹(Anthrenus verbasci)、褐粉蠹(Lyctus brunneus)、杂拟谷盗(Triboliumconfusum)、Medythia nigrobilineata、葡萄虎天牛(Xylotrechus pyrrhoderus)、黄瓜跳甲(Epitrix cucumeris)、纵坑切梢小蠹(Tomicus piniperda)、松墨天牛(Monochamusalternatus)、日本豆金龟(Popillia japonica)、豆芜青(Epicauta gorhami)、玉米象(Sitophilus zeamais)、桃实象甲(Rhynchites heros)、蔬菜叶象甲(Listroderescostirostris)、四纹豆象(Callosobruchus maculatus)、Phyllobius armatus、梨花象(Anthonomus pomorum)、铜绿里叶甲(Linaeidea aenea)和墨西哥棉铃象(Anthonomusgrandis)等。
作为双翅目(Diptera)害虫,例如可举出:淡色库蚊(Culex pipiens pallens)、甜菜潜叶蝇(Pegomya hyoscyami)、莴苣南美斑潜蝇(Liriomyza huidobrensis)、家蝇(Muscadomestica)、稻黄潜蝇(Chlorops oryzae)、稻茎毛眼水蝇(Hydrellia sasakii)、苜蓿斑潜蝇(Agromyza oryzae)、小灰毛眼水蝇(Hydrellia griseola)、小灰毛眼水蝇(Hydrelliagriseola)、菜豆蛇潜蝇(Ophiomyia phaseoli)、瓜实蝇(Dacus cucurbitae)、斑翅果蝇(Drosophila suzukii)、本樱桃实蝇(Rhacochlaena japonica)、厩腐蝇(Muscinastabulans)、东亚异蚤蝇(Megaselia spiracularis)等蚤蝇类、毛蠓(Clogmiaalbipunctata)、稻大蚊(Tipula aino)、黑花蝇(Phormia regina)、三带喙库蚊(Culextritaeniorhynchus)、中华按蚊(Anopheles sinensis)、Hylemya brassicae、椒干瘿蚊(Asphondylia sp.)、灰地种蝇(Delia platura)、葱地种蝇(Delia antiqua)、樱桃实蝇(Rhagoletis cerasi)、地下家蚊(Culex pipiens molestus Forskal)、地中海实蝇(Ceratitis capitata)、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(Chromatomyiahorticola)、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(Liriomyzatrifolii)、美洲斑潜蝇(Liriomyza sativae)、桔小实蝇(Dacus dorsalis)、蜜柑大实蝇(Dacus tsuneonis)、麦红吸浆虫(Sitodiplosis mosellana)、Meromuza nigriventris、按实蝇(Anastrepha ludens)和苹果实蝇(Rhagoletis pomonella)等。
作为膜翅目(Hymenoptera)害虫,例如可举出:短剌棱胸切叶蚁(Pristomyrmexpungens)、肿腿蜂科类、法老蚁(Monomorium pharaohnis)、宽结大头蚁(Pheidole noda)、芜菁叶蜂(Athalia rosae)、栗瘿蜂(Dryocosmus kuriphilus)、日本黑褐蚁(Formicafusca japonica)、胡蜂类、Athalia infumata infumata、月季三节叶蜂(Arge pagana)、日本菜叶蜂(Athalia japonica)、Acromyrmex spp.、红火蚁(Solenopsis spp.)、苹果三节叶蜂(Arge mali)和无毛凹臭蚁(Ochetellus glaber)等。
作为直翅目(Orthoptera)害虫,例如可举出:南方稻草螽(Homorocoryphuslineosus)、蝼蛄属(Gryllotalpa sp.)、Oxya hyla intricata、小翅稻蝗(Oxyayezoensis)、东亚飞蝗(Locusta migratoria)、日本稻蝗(Oxya japonica)、Homorocoryphus jezoensis和黄脸油葫芦(Teleogryllus emma)等。
作为缨翅目害虫,例如可举出:红带滑胸针蓟马(Selenothrips rubrocinctus)、稻蓟马(Stenchaetothrips biformis)、稻管蓟马(Haplothrips aculeatus)、Ponticulothrips diospyrosi、亮蓟马(Thrips flavus)、玉米黄呆蓟马(Anaphothripsobscurus)、樟管滑蓟马(Liothrips floridensis)、唐菖蒲简蓟马(Thrips simplex)、黑毛蓟马(Thrips nigropilosus)、温室蓟马(Heliothrips haemorrhoidalis)、桑伪棍蓟马(Pseudodendrothrips mori)、腹小头蓟马(Microcephalothrips abdominalis)、帕氏毛管蓟马(Leeuwenia pasanii)、Litotetothrips pasaniae、柑橘蓟马(Scirtothrips citri)、中华简管蓟马(Haplothrips chinensis)、豆喙蓟马(Mycterothrips glycines)、Thripssetosus、茶黄硬蓟马(Scirtothrips dorsalis)、茶棍蓟马(Dendrothrips minowai)、Haplothrips niger、烟蓟马(Thrips tabaci)、葱韭蓟马(Thrips alliorum)、黄胸蓟马(Thrips hawaiiensis)、豆简管蓟马(Haplothrips kurdjumovi)、袖指蓟马(Chirothripsmanicatus)、花蓟马(Frankliniella intonsa)、色蓟马(Thrips coloratus)、西花蓟马(Franklinella occidentalis)、棕榈蓟马(Thrips palmi)、百合蓟马(Frankliniellalilivora)和百合滑管蓟马(Liothrips vaneeckei)等。
作为蜱螨目害虫,例如可举出:红纤沙螨(Leptotrombidium akamushi)、卢氏叶螨(Tetranychus ludeni)、变异革蜱(Dermacentor variabilis)、截形叶螨(Tetranychustruncatus)、柏氏禽刺螨(Ornithonyssus bacoti)、犬脂螨(Demodex canis)、山楂叶螨(Tetranychus viennensis)、神泽叶螨(Tetranychus kanzawai)、血红扇头蜱(Rhipicephalus sanguineus)等的真蜱类、马六甲肉食螨(Cheyletus malaccensis)、腐食酪螨(Tyrophagus putrescentiae)、粉尘螨(Dermatophagoides farinae)、赤背蜘蛛(Latrodectus hasseltii)、中国台湾革蜱、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)、Eriophyes chibaensis、人疥螨(Sarcoptes scabiei)、长角血蜱(Haemaphysalis longicornis)、肩突硬蜱(Ixodesscapularis)、似食酪螨(Tyrophagus similis)、普通肉食螨(Cheyletus eruditus)、柑桔全爪螨(Panonychus citri)、Cheyletus moorei、紫红短须螨(Brevipalpus phoenicis)、犬猫耳螨(Octodectes cynotis)、屋尘螨(Dermatophagoides ptrenyssnus)、褐黄血蜱(Haemaphysalis flava)、卵形硬蜱(Ixodes ovatus)、Phyllocoptruta citri、Aculusschlechtendali、苹果全爪螨(Panonychus ulmi)、美洲钝眼蜱(Amblyomma americanum)和鸡皮刺螨(Dermanyssus gallinae)、Rhyzoglyphus robini、Sancassania sp.等。
作为等翅目害虫,例如可举出:Reticulitermes miyatakei、小楹白蚁(Incisitermes minor)、中国台湾乳白蚁、Hodotermopsis japonica、散白蚁(Reticulitermes sp.)、黄胸散白蚁(Reticulitermes flaviceps amamianus)、古希美树白蚁(Glyptotermes kushimensis)、广州乳白蚁(Coptotermes guangzhoensis)、恒春新白蚁(Neotermes koshunensis)、Glyptotermes kodamai、赤树白蚁(Glyptotermessatsumensis)、截头堆砂白蚁(Cryptotermes domesticus)、黑翅土白蚁、Glyptotermesnakajimai、新渡户近扭白蚁(Pericapritermes nitobei)和栖北散白蚁(Reticulitermessperatus)等。
作为蜚蠊目害虫,例如可举出:黑胸大蠊(Periplaneta fuliginosa)、德国小蠊(Blattella germanica)、东方蜚蠊(Blatta orientalis)、褐斑大蠊(Periplanetabrunnea)、拟德国小蠊(Blattella lituricollis)、日本大蠊(Periplaneta japonica)和美洲大蠊(Periplaneta americana)等。
作为蚤目,例如可举出:人蚤(Pulex irritans)、猫蚤(Ctenocephalides felis)和鸡角叶蚤(Ceratophyllus gallinae)等。
作为线虫类,例如可举出:草莓芽线虫(Nothotylenchus acris)、水稻干尖线虫(Aphelenchoides besseyi)、穿刺短体线虫(Pratylenchus penetrans)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、马铃薯金线虫(Globodera rostochiensis)、爪哇根结线虫(Meloidogyne javanica)、大豆胞囊线虫(Heterodera glycines)、咖啡短体线虫(Pratylenchus coffeae)、落选短体线虫(Pratylenchus neglectus)和柑桔根线虫(Tylenchus semipenetrans)等。
作为软体动物类,例如可举出:福寿螺(Pomacea canaliculata)、非洲大蜗牛(Achatina fulica)、双线蛞蝓(Meghimatium bilineatum)、Lehmannina valentiana、黄蛞蝓(Limax flavus)和Acusta despecta sieboldiana等。
此外,本发明的用于农业园艺的杀虫剂对作为其它害虫的番茄潜麦蛾(Tutaabsoluta)具有较强的杀虫效果。
此外,作为防治对象之一的动物寄生性的蜱螨,例如可举出:微小牛蜱(Boophilusmicroplus)、血红扇头蜱(Rhipicephalus sanguineus)、长角血蜱(Haemaphysalislongicornis)、褐黄血蜱(Haemaphysalis flava)、何氏血蜱(Haemaphysaliscampanulata)、嗜群血蜱(Haemaphysalis concinna)、日本血蜱(Haemaphysalisjaponica)、北岗血蜱(Haemaphysalis kitaokai)、Haemaphysalis ias、卵形硬蜱(Ixodesovatus)、Ixodes nipponensis、全沟硬蜱(Ixodes persulcatus)、龟甲形钝眼蜱(Amblyomma testudinarium)、Haemaphysalis megaspinosa、网纹革蜱(Dermacentorreticulatus)和中国台湾革蜱这样的蜱类;鸡皮刺螨(Dermanyssus gallinae)、北方刺脂螨(Ornithonyssus sylviarum)和囊禽刺螨(Ornithonyssus bursa)这样的林禽刺螨类(Northernfowl mite);危鸡犹沙螨(Eutrombicula wichmanni)、红纤恙螨(Leptotrombidium akamushi)、苍白纤恙螨(Leptotrombidium pallidum)、富士纤恙螨(Leptotrombidium fuji)、Leptotrombidium tosa、秋收恙螨(Neotrombiculaautumnalis)、阿[耳弗雷杜热斯]氏真恙螨(Eutrombicula alfreddugesi)和宫川合轮螨(Helenicula miyagawai)这样的恙螨类;牙氏姬螯螨(Cheyletiella yasguri)、兔皮姬螯螨(Cheyletiella parasitivorax)和布氏姬螯螨(Cheyletiella blakei)这样的姬螯螨类;兔痒螨(Psoroptes cuniculi)、牛足螨(Chorioptes bovis)、猫犬耳螨(Otodectescynotis)、人疥螨(Sarcoptes scabiei)和猫背肛螨(Notoedres cati)这样的疥螨类;以及犬脂螨(Demodex canis)这样的毛囊脂螨类等。
作为其他防治对象的蚤,例如可举出属于蚤目(Siphonaptera)的外部寄生性无翅昆虫,更具体而言,可举出属于蚤科(Pulicidae)和欧洲鼠蚤科(Ceratephyllus)等的蚤类。作为属于蚤科的蚤类,例如可举出:犬栉首蚤(Ctenocephalides canis)、猫蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、鸡蚤(Echidnophaga gallinacea)、印鼠客蚤(Xenopsylla cheopis)、缓慢细蚤(Leptopsylla segnis)、具带病蚤(Nosopsyllusfasciatus)和不等单蚤(Monopsyllus anisus)等。
此外,作为其他防治对象的外部寄生生物,例如可举出:牛盲虱(Haematopinuseurysternus)、马吸血虱(Haematopinus asini)、羊虱(Dalmalinia ovis)、长鼻牛虱(Linognathus vituli)、猪血虱(Haematopinus suis)、阴虱(Phthirus pubis)和头虱(Pediculus capitis)这样的吸虱类;以及犬啮毛虱(Trichodectes canis)这样的咬虱类、三角虻(Tabanus trigonus)、虚库蠓(Culicoides schultzei)和饰蚋(Simulium ornatum)这样的吸血性双翅目害虫等。此外,作为内部寄生生物,例如可举出:肺虫、鞭虫(Trichuris)、结节线虫、胃内寄生虫、蛔虫和丝虫类这样的线虫类;刺猬绦虫(Spirometraerinaceieuropaei)、阔节裂头绦虫(Diphyllobothrium latum)、复孔绦虫(Dipylidiumcaninum)、多头绦虫(Taenia multiceps)、细粒棘球绦虫(Echinococcus granulosus)和多房棘球绦虫(Echinococcus multilocularis)这样的绦虫类;日本血吸虫(Schistosomajaponicum)和片吸虫(Fasciola hepatica)这样的吸虫类;以及球虫、疟原虫(Plasmodiummalariae)、肠内肉孢子虫、弓形虫、隐孢子虫这样的原生动物等。
作为内部寄生生物,更详细地,例如可举出如下,
嘴刺目(Enoplida)寄生虫:鞭虫亚属(鞭虫)(Trichuris spp.)、毛细线虫亚属(毛细线虫)(Capillaria spp.)、Trichomosoides spp.、旋毛虫亚属(Trichinella spp.),小杆目(Rhabditia)例如微线虫亚属(Micronema spp.)、类圆线虫亚属(Strongyloidesspp.),圆线虫目(Strongylida)例如圆形线虫亚属(圆线虫)(Stronylus spp.)、三齿线虫亚属(Triodontophorus spp.)、食管齿线虫亚属(Oesophagodontus spp.)、毛线线虫亚属(Trichonema spp.)、似六齿线虫亚属(Gyalocephalus spp.)、柱咽线虫亚属(Cylindropharynx spp.)、杯口线虫亚属(Poteriostomum spp.)、Cyclococercus spp.、杯冠线虫亚属(Cylicostephanus spp.)、结节线虫亚属(Oesophagostomum spp.)、夏氏线虫亚属(Chabertia spp.)、牙冠线虫亚属(猪肾虫)(Stephanurus spp.)、钩虫亚属(十二指肠钩虫)(Ancylostoma spp.)、Uncinaria spp.、仰口线虫亚属(Bunostomum spp.)、球头线虫亚属(Globocephalus spp.)、比翼亚属(交合线虫)(Syngamus spp.)、杯口吸虫亚属(Cyathostoma spp.)、后圆线虫亚属(Metastrongylus spp.)、网尾线虫亚属(Dictyocaulus spp.)、缪勒线虫亚属(Muellerius spp.)、原圆线虫亚属(Protostrongylus spp.)、新圆线虫亚属(Neostrongylus spp.)、囊尾线虫亚属(Cystocaulus spp.)、肺圆线虫亚属(Pneumostrongylus spp.)、Spicocaulus spp.、麂圆线虫亚属(Elaphostrongylus spp.)、副麂圆线虫亚属(Parelaphostrongylus spp.)、环体线虫亚属(Crenosoma spp.)、Parelaphostrongylus spp.、住血线虫亚属(Angiostrongylus spp.)、猫圆线虫亚属(Aelurosutrongylus spp.)、类丝虫亚属(Filaroides spp.)、副类丝虫亚属(Parafilaroides spp.)、毛圆线虫亚属(Trichostrongylus spp.)、血矛线虫亚属(捻转血矛线虫)(Haemonchus spp.)、胃线虫亚属(Ostertagia spp.)、马歇尔线虫亚属(Marshallagia spp.)、古柏线虫属(Cooperiaspp.)、细颈线虫亚属(线虫)(Nematodirus spp.)、猪圆线虫亚属(Hyostrongylus spp.)、尖柱线虫亚属(Obeliscoides spp.)、裂口线虫亚属(Amidostomum spp.)、沃鲁线虫亚属(Ollulanus spp.)等;
尖尾目(Oxyurida)寄生虫:尖尾线虫亚属(Oxyuris spp.)、蛲虫亚属(蛲虫)(Enterobius spp.)、栓尾线虫亚属(Passalurus spp.)、管状线虫亚属(Syphacia spp.)、无刺线虫亚属(Aspiculuris spp.)、异刺线虫亚属(Heterakis spp.)等;
蛔虫目(Ascaridia)寄生虫:蛔虫亚属(Ascaris spp.)、弓蛔线虫亚属(Toxascaris spp.)、弓蛔虫亚属(犬蛔虫)(Toxocara spp.)、副蛔虫亚属(马蛔虫)(Parascaris spp.)、异尖线虫亚属(Anisakis spp.)、鸡蛔虫亚属(Ascaridia spp.),旋尾目(旋尾线虫类)(Spirurida)例如颚口线虫亚属(Gnathostoma spp.)、泡翼线虫亚属(Physaloptera spp.)、吸吮线虫亚属(Thelazia spp.)、筒线虫亚属(Gongylonema spp.)、丽线虫亚属(Habronema spp.)、斯氏副柔线虫亚属(Parabronema spp.)、德拉西线虫亚属(Draschia spp.)、龙线虫亚属(Dracunculus spp.)等;
丝虫目(Filariida):冠丝虫亚属(Stephanofilaria spp.)、副丝虫亚属(Parafilaria spp.)、腹腔丝虫亚属(Setaria spp.)、阿丝虫亚属(Loa spp.)、恶丝虫亚属(犬恶丝虫)(Dirofilaria spp.)、光丝虫亚属(Litomosoides spp.)、布鲁丝虫亚属(Brugia spp.)、吴策线虫亚属(丝虫)(Wuchereria spp.)、盘尾丝虫亚属(Onchocercaspp.)等;
巨吻目(Gigentorhynchida):细颈棘头虫亚属(Filicollis spp.)、念珠棘虫亚属(Moniliforumis spp.)、巨吻棘虫亚属(Macracanthorhynchus spp.)、前睾棘头虫亚属(Prosthenorchis spp.)等。
以本发明的通式(1)表示的苯并咪唑化合物或其盐类为有效成分的内部寄生虫防治剂,不仅对栖息于中间宿主和最终宿主的体内的寄生虫表现出效果,而且对保虫宿主生物体内的寄生虫也表现出效果。此外,本发明的通式(1)表示的苯并咪唑化合物或其盐类在寄生虫的整个发育阶段均表现出效果。例如,在原虫类中为包囊、前包囊型、营养型或无性生殖期的分裂体、阿米巴体、有性生殖期的配子母细胞、配子、融合体、孢子体等。在线虫类中为卵、幼虫、成虫。此外,本发明的化合物不仅可消灭生物体内的寄生虫,而且可通过施用于作为感染路径的环境中来预防性地防止寄生虫的感染。可预防下述感染于未然,例如:来自旱田、公园的土壤的土壤传播感染、来自河川、湖沼、湿地、水田等水系的经皮感染、来自犬、猫等动物的粪便的经口感染、来自海水鱼、淡水鱼、甲壳类、贝类、家畜的生肉等的经口感染、来自蚊、虻、蝇、蟑螂、螨、蚤、虱、猎蝽、恙虫等的感染等。
当使用本发明化合物来防治家哺乳动物和鸟类的外部或内部寄生虫时,可将有效量的本发明化合物与制剂用添加物同时通过下述方式进行给药:口服给药;注射(肌肉内、皮下、静脉内、腹腔内)等非口服给药;浸渍、喷涂、入浴、洗涤、泼浇(pouring-on)、点涂(spotting-on)以及撒粉(dusting)等透皮给药;鼻腔给药。此外,本发明化合物可通过使用了细片、板、带、项圈、耳标(ear mark)、肢带(limb band)、标记装置等的成形制品来给药。当给药时,可将本发明化合物制成适合给药路径的任意剂型。
作为任意剂型,可举出:粉剂、粒剂、可湿性粉剂、颗粒剂、片剂、大丸剂、胶囊剂、包含活性化合物的成形制品等固体制剂;注射用液剂、口服用液剂、皮肤上或体腔中使用的液剂;泼浇(Pour-on)剂、点涂(Spot-on)剂、悬浮剂(Flowable agent)、乳剂等溶液制剂;软膏剂、凝胶等半固体制剂等。
固体制剂可主要用于口服给药或用水等稀释而用于透皮给药或环境处理。固体制剂可通过下述方式来制备:添加活性化合物并在需要时添加辅助剂与适当的赋形剂混合,制成期望的形状。作为适当的赋形剂,例如可举出:碳酸盐、碳酸氢盐、磷酸盐、氧化铝、二氧化硅、粘土等无机物质;糖、纤维素、粉碎的谷物、淀粉等有机物质。
注射用液剂可以给药至静脉内、肌肉内和皮下,注射用液剂可通过将活性化合物溶解至适当的溶剂中,并且在需要时添加增溶剂、酸、碱、缓冲盐、抗氧化剂和保护剂等添加剂来制备。作为适当的溶剂,可举出:水、乙醇、丁醇、苯甲醇、丙三醇、丙二醇、聚乙二醇、N-甲基吡咯烷酮以及这些的混合物、生理上允许的植物油、适合注射的合成油等。作为增溶剂,可举出:聚乙烯吡咯烷酮、聚氧乙基化蓖麻油和聚氧乙基化山梨糖醇酐酯等。保护剂包括苯甲醇、三氯丁醇、对羟基苯甲酸酯和正丁醇等。
口服液剂可以直接或稀释后给药。可以与注射用液剂同样的方式制备。
悬浮剂、乳剂等可直接给药、或稀释后经皮性地给药或通过环境处理给药。
皮肤上使用的液剂可通过下述方式给药:泼浇、铺开、擦、喷雾、散布或通过浸渍(浸渍、入浴或洗涤)涂布。这些液剂可以与注射用液剂同样的方式制备。
可将泼浇(Pour-on)剂和点涂(Spot-on)剂泼浇或喷雾至限定的皮肤位置,由此使活性化合物浸渍皮肤并且全身性地起作用。泼浇剂和点涂剂可通过将有效成分溶解至适当的皮肤适合性溶剂或溶剂混合物、使其悬浮或乳化来制备。在需要时,可以添加表面活性剂、着色剂、吸收促进物质、抗氧化剂、光稳定剂和粘接剂等辅助剂,作为溶剂,可举出:水、链烷醇、乙二醇、聚乙二醇、聚丙二醇、丙三醇、苯甲醇、苯乙醇、苯氧乙醇、乙酸乙酯、乙酸丁酯、苯甲酸苄酯、二丙二醇单甲醚、二乙二醇单丁醚、丙酮、甲基乙基酮、芳香族和/或脂肪族烃、植物油或合成油、(二甲基甲酰胺)DMF、液体石蜡、轻质液体石蜡、聚硅氧烷、二甲基乙酰胺、N-甲基吡咯烷酮或2,2-二甲基-4-氧基-亚甲基-1,3-二氧戊环。吸收促进物质可举出:(二甲亚砜)DMSO、肉豆蔻酸异丙酯、壬酸二丙二醇、硅油、脂肪族酯、甘油三酯和脂肪醇。抗氧化剂可举出:亚硫酸盐、偏重亚硫酸盐、抗坏血酸、丁基羟基甲苯、丁基羟基苯甲醚和生育酚。
乳剂可口服给药、透皮给药或注射给药。乳剂可通过下述方式来制备:使有效成分溶解于疏水相或亲水相中,之后通过适当的乳化剂并在需要时进一步与着色剂、吸收促进物质、保护剂、抗氧化剂、遮光剂和增稠剂等辅助剂一起与其他相溶剂进行均质化。
作为疏水相(油),可举出:石蜡油、硅油、芝麻油、杏仁油、蓖麻油、合成甘油三酯、硬脂酸乙酯、己二酸二正丁酯、Hexyl deurylate(デウリル酸ヘキシル)、二丙二醇壬酸酯、支链状的短链长脂肪酸与链长C16~C18的饱和脂肪酸形成的酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、链长C12~C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙酯、油酸油酯、油酸癸酯、油酸乙酯、乳酸乙酯、蜡状脂肪酸酯、苯二甲酸二丁酯、己二酸二异丙酯、异十三烷醇、2-辛基十二烷醇、鲸蜡硬脂醇、油醇。
作为亲水相,可举出:水、丙二醇、丙三醇、山梨糖醇。
作为乳化剂,可举出:聚氧乙基化蓖麻油、聚氧乙基化山梨糖醇酐单烯烃酸酯、山梨糖醇酐单硬脂酸酯、丙三醇单硬脂酸酯、聚氧乙基硬脂酸酯、烷基酚聚二醇醚等非离子性表面活性剂;N-月桂基β-亚氨基二丙酸二钠、卵磷脂等两性表面活性剂;月桂基硫酸钠、脂肪醇硫酸醚、单/二烷基聚二醇正磷酸酯的单乙醇胺盐等阴离子性表面活性剂;鲸蜡基三甲基氯化铵等阳离子性表面活性剂等。
作为其他辅助剂,可举出:羧甲基纤维素、甲基纤维素、聚丙烯酸酯、藻酸盐(Alginate)、明胶、阿拉伯树胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯基醚、马来酸酐的共聚物、聚乙二醇、蜡、胶体状二氧化硅。
半固体制剂可通过涂布至皮肤上或铺开,或导入体腔中来给药。凝胶可通过下述方式制备:对于注射用液剂,向如上所述制备的溶液中添加足够的增稠剂,以产生具有软膏状的粘稠性的透明物质。
在将本发明的内部寄生虫防治剂用作属于人类以外的哺乳类或鸟类的动物的药品的情况下,有效成分的最佳量(有效量)根据治疗或预防的类别、感染寄生虫的种类、感染的类型和程度、剂型等而发生变化,通常在口服给药的情况下,每天约0.0001~10000mg/kg体重的范围内。在非口服给药的情况下,每天约.0001~10000mg/kg体重的范围内,单次或多次给药。
本发明的内部寄生虫防治剂中的有效成分的浓度通常为0.001~100质量%,优选为0.001~99%,更优选为约0.005~20质量%。本发明的内部寄生虫防治剂可以是直接给药的组合物,也可以是在使用时将其稀释至适当的浓度而使用的高浓度组合物。
此外,为了增强或补充本发明的内部寄生虫防治剂的效果,可与现有的内部寄生虫防治剂组合使用。在组合使用的情况下,可以是在给药前混合2种以上的有效成分而得到的制剂,也可以是分别给药2种以上的不同制剂。
由于以本发明的通式(1)表示的苯并咪唑化合物或其盐类为有效成分的用于农业园艺的杀虫杀螨剂,对损害水田作物、旱田作物、果树、蔬菜、其它作物和花卉等的所述害虫具有显著的防治效果,因此根据预测发生害虫的时期来在发生害虫前或确认发生的时间点对育苗设施、水田、旱田、果树、蔬菜、其它作物、花卉等的种子、水田水、茎叶或土壤等的栽培载体等进行处理,来实现本发明的用于农业园艺的杀虫杀螨剂的期望效果。其中,优选的使用方式是:通过对作物、花卉等的育苗土壤、移植时的种植孔土壤、植物的根、灌溉水、水耕栽培中的栽培水等进行处理、经过土壤或不经过土壤而由根吸收本发明化合物而利用了所谓的渗透转移性。
可使用本发明的用于农业园艺的杀虫杀螨剂的有用植物没有特别限定,例如可举出:谷类(例如,稻子、大麦、小麦、黑麦、燕麦、玉米等)、豆类(大豆、红豆、蚕豆、豌豆、菜豆、花生等)、果树·果实类(苹果、柑橘类、梨、葡萄、桃子、李子、樱桃、胡桃、栗子、杏仁、香蕉等)、叶·果菜类(卷心菜、番茄、菠菜、西兰花、生菜、洋葱、葱(胡葱、冬葱)、甜椒、茄子、草莓、胡椒、秋葵、韭菜等)、根茎类蔬菜(胡萝卜、马铃薯、甘薯、芋头、萝卜、芜菁、藕、牛蒡、大蒜、薤等)、加工用作物(棉、麻、甜菜根、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、真桑瓜、甜瓜等)、牧草类(鸭茅、高粱、梯牧草、三叶草、紫花苜蓿等)、结缕草类(高丽结缕草、糠穗草(Agrostis)等)、香料等观赏用作物(薰衣草、迷迭香、百里香、荷兰芹、胡椒、生姜等)、花卉类(菊花、玫瑰、康乃馨、兰花、郁金香、百合等)、庭园树木(银杏、樱花类、珊瑚木等)、林木(冷杉类、鱼鳞云杉类、松类、柏、杉、日本扁柏、桉等)等植物。
所述“植物”还包含通过对除草剂具有抗性的经典育种法或基因重组技术而被赋予了抗性的植物,所述除草剂包含:异噁唑草酮等HPPD抑制剂、咪草烟、噻吩磺隆等ALS抑制剂、草甘膦等EPSP合成酶抑制剂、草铵膦等谷氨酰胺合成酶抑制剂、烯禾啶等乙酰辅酶A羧化酶抑制剂、溴苯腈、麦草畏、2,4-D等。
作为通过经典育种法被赋予了抗性的“植物”的实例,可举出对咪草烟等咪唑啉酮类ALS抑制型除草剂具有抗性的油菜籽、小麦、向日葵、水稻,并已经以Clearfield(注册商标)的商品名贩售。可举出同样通过经典育种法而对噻吩磺隆等磺酰脲类ALS抑制型除草剂具有抗性的大豆,已经以STS大豆的商品名贩售。作为同样通过经典育种法赋予了对三酮肟(Trion oxime)类、芳氧基苯氧基丙酸类除草剂等乙酰辅酶A羧化酶抑制剂的抗性的植物的实例,可举出SR玉米(Cone)等。
此外,被赋予了对乙酰辅酶A羧化酶抑制剂的抗性的植物记载于美利坚合众国国家科学院院刊(Proceedings of the National Academy of Sciences of the UnitedStates of America,Proc.Natl.Acad.Sci.USA)87卷,7175~7179页(1990年)等。此外,对乙酰辅酶A羧化酶抑制剂具有抗性的变异乙酰辅酶A羧化酶已经报告于杂草科学(WeedScience)53卷,728~746页(2005年)等,可通过基因重组技术将这样的变异乙酰辅酶A羧化酶基因导入植物,或通过将与抗性赋予有关的变异导入植物乙酰辅酶A羧化酶,来得到对乙酰辅酶A羧化酶抑制剂具有抗性的植物,并且,通过以嵌合修复技术(chimeraplasty technology)(Gura T.1999.Repairing the Genome's Spelling Mistakes.Science 285:316-318.)为代表的将导入有碱基取代变异的核酸导入植物细胞内从而在植物的乙酰辅酶A羧化酶基因、ALS基因等中部位特异性地导入氨基酸取代变异的技术,而能够得到对乙酰辅酶A羧化酶抑制剂、ALS抑制剂等具有抗性的植物,对于这些植物也可使用本发明的用于农业园艺的杀虫杀螨剂。
此外,作为基因重组植物中表达的毒素,可举出:源自蜡样芽孢杆菌、日本甲虫芽孢杆菌的杀虫蛋白;源自苏云金芽孢杆菌的Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C等δ-内毒素、VIP1、VIP2、VIP3或VIP3A等杀虫蛋白;源自线虫的杀虫蛋白;蝎子毒素、蜘蛛毒素、蜂毒素或昆虫特异性神经毒素等由动物产生的毒素;丝状菌类毒素;植物凝集素;凝集素;胰朊酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯块茎储藏蛋白(Patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂等蛋白酶抑制剂;蓖麻毒素、玉米-RIP、红豆碱、绛酚(Rufin)、肥皂草素、泻根(Bryonia dioica)等核糖体失活蛋白(RIP);3-羟基类固醇氧化酶、蜕化类固醇-UDP-葡萄糖基转移酶、胆固醇氧化酶等类固醇代谢酶;蜕皮激素抑制剂;HMG-CoA还原酶;钠通道、钙通道抑制剂等离子通道抑制剂;保幼激素酯酶;利尿激素受体;芪合酶(Stilbene synthase);联苄合酶;几丁质酶;葡聚糖酶等。
此外,作为这样的基因重组植物中表达的毒素,还包含:Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9C、Cry34Ab或Cry35Ab等δ-内毒素蛋白、VIP1、VIP2、VIP3或VIP3A等杀虫蛋白的混合毒素、部分缺失的毒素、经过修饰的毒素。使用重组技术,通过这些蛋白的不同的域的新组合来产生混合毒素。作为部分缺失的毒素,已知有氨基酸序列的一部分缺失的Cry1Ab。作为经过修饰的毒素,天然型毒素的一个或多个氨基酸被取代。
这些毒素的实例和能够合成这些毒素的重组植物记载于EP-A-0374753、WO93/07278、WO95/34656、EP-A-0427529、EP-A-451878、WO03/052073等。
这些重组植物中包含的毒素特别是赋予了植物对甲虫目害虫、半翅目害虫、双翅目害虫、鳞翅目害虫、线虫类的抗性。本发明的用于农业园艺的杀虫杀螨剂可与这些技术组合使用或系统性地使用。
为了防治各种害虫,将有效防治害虫或线虫的量的本发明的用于农业园艺的杀虫杀螨剂直接施用或用水等适宜稀释或以悬浮形式用于预测发生该害虫和线虫的植物即可,例如针对果树、谷类、蔬菜等中发生的害虫和线虫,除了散布于茎叶部之外,还可将种子浸渍于药剂中、对种子进行粉衣(Seed coat)、进行过氧化钙处理等种子处理、土壤全层混合、条施、床土混合、穴盘苗处理、种植孔处理、根系处理、施顶肥、水稻的箱处理、水面施用等对土壤等进行处理而能够由根吸收,来使用本发明的用于农业园艺的杀虫杀螨剂。此外,还可通过在营养液(水耕)栽培中向营养液中施用、烟熏或注入树干等来使用。
此外,将有效防治害虫的量的本发明的用于农业园艺的杀虫杀螨剂直接或用水等适宜稀释或以悬浮形式用于预测发生该害虫的场所即可,例如除了散布于储粮害虫、房屋害虫、卫生害虫、森林害虫等之外,还可用作对房屋建材的涂布、烟熏、诱饵等。
作为种子处理的方法,例如可举出:将液态或固体状的制剂以稀释或未稀释的液体状态浸渍种子以使药剂渗透的方法;将固体制剂或液态制剂与种子混合并进行粉衣处理以附着于种子的表面的方法;与树脂、聚合物等附着性的载体混合来包覆种子的方法;在种植的同时散布于种子附近的方法等。
进行该种子处理的“种子”是指植物的繁殖中使用的栽培初期的植物体,例如除种子之外,还可举出:球根、块茎、种薯、植物芽、珠芽、鳞茎或插枝栽培用的营养繁殖用的植物体。
在实施本发明的使用方法的情况下植物的“土壤”或“栽培载体”是表示用于栽培作物的支撑体,特别是表示使根生长的支撑体,材质没有特别限定,是植物可生长的材质即可,可以是所谓的土壤、育苗垫、水等,作为具体的原材料,例如可以是沙子、轻石、蛭石、硅藻土、琼脂、凝胶状物质、高分子物质、岩棉、玻璃棉、木屑、树皮等。
针对作物茎叶部或储粮害虫、房屋害虫、卫生害虫或森林害虫等散布的方法,可举出:将乳剂、悬浮剂等液体制剂或可湿性粉剂或颗粒状可湿性粉剂等固体制剂用水适宜稀释并散布的方法、将粉剂进行散布的方法或烟熏等。
作为向土壤施用的方法,例如可举出:将液体制剂用水稀释或未稀释并施用于植物体的根或育苗用苗床等的方法、将粒剂散布至植物体的根或用于育苗的苗床等的方法、在播种前或移植前散布粉剂、可湿性粉剂、颗粒状可湿性粉剂、粒剂等并与整个土壤混合的方法、在播种前或种植植物体前将粉剂、可湿性粉剂、颗粒状可湿性粉剂、粒剂等散布于种植孔、作条等的方法等。
作为将水稻施用于育苗箱的方法,剂型可根据例如播种时施用、绿化期施用、移植时施用等施用时期而不同,以粉剂、颗粒状可湿性粉剂、粒剂等剂型施用即可。可通过与栽培土混合来施用,可进行栽培土和粉剂、颗粒状可湿性粉剂或粒剂等的混合,例如进行床土混合、覆土混合、与整个栽培土的混合等。可以简单地将栽培土与各种制剂交替地形成层状来施用。
作为施用于水田的方法,通常将大粒剂(Jumbo)、包装剂、粒剂、颗粒状可湿性粉剂等固体制剂、流动剂、乳剂等液体状制剂散布于水淹状态的水田。此外,可在插秧时,将适当的制剂直接或与肥料混合后散布并注入土壤中。此外,可通过在水口、灌溉装置等水田中的水的流入源处利用乳剂、流动剂等药液并伴随水的供给而省力地施用。
在旱田作物中,可在播种至育苗期间,对种子或植物体附近的栽培载体等进行处理。在直接播种于旱田的植物中,除了直接对种子进行处理之外,优选对栽培中的植物的根进行处理。可使用粒剂进行散布处理或用水稀释或未稀释的药剂以液态进行灌溉处理。将粒剂与播种前的栽培载体混合后进行播种也是优选的处理。
作为进行移植的栽培植物的播种、育苗期的处理,除了直接对种子进行处理之外,优选对育苗用苗床进行制成液态的药剂的灌溉处理或粒剂的散布处理。此外,在定植时用粒剂对种植孔进行处理或将粒剂与移植位置附近的栽培载体混合也是优选的处理。
通常,根据农药制剂上的常规方法将本发明的用于农业园艺的杀虫杀螨剂制成易于使用的形状来使用。
即,就本发明的通式(1)表示的苯并咪唑化合物或其盐类而言,使其溶解、分离、悬浮、混合、浸渍、吸附或附着于适当的不活泼载体或根据需要与辅助剂一起以适当的比例混合后再溶解、分离、悬浮、混合、浸渍、吸附或附着于适当的不活泼载体以制成适宜的剂型来使用即可,例如制成悬浮剂、乳剂、液剂、可湿性粉剂、颗粒状可湿性粉剂、粒剂、粉剂、片剂、包装剂等。
本发明的组合物(用于农业园艺的杀虫杀螨剂或动物寄生生物防治剂)中,除了有效成分之外,还可根据需要含有农药制剂或动物寄生生物防治剂中通常使用的添加成分。作为该添加成分,可举出:固体载体、液体载体等载体、表面活性剂、分散剂、湿润剂、粘合剂、增粘剂、增稠剂、着色剂、扩展剂、铺展剂、防冻剂、抗结块剂、崩解剂、分解抑制剂等。根据其它需要,可以将防腐剂、植物片等用作添加成分。这些添加成分可以单独使用一种并且可以组合使用两种以上。
作为固体载体,例如可举出:石英、黏土、高岭石、叶蜡石、绢云母、滑石粉、膨润土、酸性白土、硅镁土、沸石、硅藻土等天然矿物类、碳酸钙、硫酸铵、硫酸钠、氯化钾等无机盐类、合成硅酸、合成硅酸盐、淀粉、纤维素、植物粉末(例如锯末、椰子壳、玉米秸秆、烟梗等)等有机固体载体、聚乙烯、聚丙烯、聚偏二氯乙烯等塑料载体、尿素、无机空心体、塑料空心体、气相法二氧化硅(fumed silica,白炭黑)等。这些可以单独使用一种并且可以组合使用两种以上。
作为液体载体,例如可举出:甲醇、乙醇、丙醇、异丙醇、丁醇等一价醇类、乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、丙三醇等多元醇类这样的醇类、丙二醇醚等多元醇化合物类、丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮等酮类、乙醚、二噁烷、乙二醇单乙醚、二丙醚、四氢呋喃等醚类、正构烷烃、环烷、异链烷烃、煤油、矿油等脂肪族烃类、苯、甲苯、二甲苯、溶剂石脑油、烷基萘等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤代烃类、乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、己二酸二甲酯等酯类、γ-丁内酯等内酯类、二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺、N-烷基吡咯烷酮等酰胺类、乙腈等腈类、二甲亚砜等硫化物类、大豆油、菜籽油、棉籽油、蓖麻油等植物油、水等。这些可以单独使用一种并且可以组合使用两种以上。
作为用作分散剂、湿展剂的表面活性剂,例如可举出:山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福尔马林缩合物、聚氧乙烯聚氧丙烯嵌段共聚物、聚苯乙烯聚氧乙烯嵌段共聚物、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、聚氧乙烯脂肪酸双苯基醚、聚亚烷基苄基苯基醚、聚氧亚烷基苯乙烯基苯基醚、乙炔二醇、聚氧亚烷基加成乙炔二醇、聚氧乙烯醚型聚硅氧烷、酯型聚硅氧烷、氟类表面活性剂、聚氧乙烯蓖麻油、聚氧乙烯固化蓖麻油等非离子性表面活性剂、烷基硫酸盐、聚氧乙烯烷基醚硫酸盐、聚氧乙烯烷基苯基醚硫酸盐、聚氧乙烯苯乙烯基苯基醚硫酸盐、烷基苯磺酸盐、烷基芳基磺酸盐、木质素磺酸盐、烷基磺基琥珀酸盐、萘磺酸盐、烷基萘磺酸盐、萘磺酸的福尔马林缩合物的盐、烷基萘磺酸的福尔马林缩合物的盐、脂肪酸盐、聚羧酸盐、聚丙烯酸盐、N-甲基-脂肪酸肌氨酸盐、树脂酸盐、聚氧乙烯烷基醚磷酸盐、聚氧乙烯烷基苯基醚磷酸盐等阴离子性表面活性剂、月桂基胺盐酸盐、硬脂基胺盐酸盐、油胺盐酸盐、硬脂胺乙酸盐、硬脂基氨基丙基胺乙酸盐、烷基三甲基氯化铵、烷基二甲基苯扎氯铵等烷基胺盐等阳离子表面活性剂、氨基酸型或甜菜碱型等的两性表面活性剂等。这些表面活性剂可以单独使用一种并且可以组合使用两种以上。
作为粘合剂、增粘剂,例如可举出:羧甲基纤维素及其盐、糊精、水溶性淀粉、黄原胶、瓜尔豆胶、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、平均分子量6000~20000的聚乙二醇、平均分子量10万~500万的聚环氧乙烷、磷脂(例如脑磷脂、卵磷脂等)纤维素粉末、糊精、加工淀粉、聚氨基羧酸螯合物、交联聚乙烯吡咯烷酮、马来酸与苯乙烯类形成的共聚物、(甲基)丙烯酸类共聚物、包含多元醇的聚合物与二羧酸酐形成的半酯、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、烷基酚福尔马林缩合物、合成树脂乳液等。
作为增稠剂,例如可举出:黄原胶、瓜尔豆胶、Diutan gum、羧甲基纤维素、聚乙烯吡咯烷酮、羧乙烯基聚合物、丙烯酸类聚合物、淀粉化合物、多糖类这样的水溶性高分子、高纯度膨润土、气相法二氧化硅(fumed silica、白炭黑)这样的无机微粉等。
作为着色剂,例如可举出:氧化铁、氧化钛、普鲁士蓝这样的无机颜料、茜素染料、偶氮染料、金属酞菁染料这样的有机染料等。
作为防冻剂,例如可举出:乙二醇、二乙二醇、丙二醇、丙三醇等多元醇类等。
作为用于防止结块、促进崩解的辅助剂,例如可举出:淀粉、海藻酸、甘露糖、半乳糖等多糖类、聚乙烯吡咯烷酮、气相法二氧化硅(fumed silica、白炭黑)、酯胶、石油树脂、三聚磷酸钠、六偏磷酸钠、硬脂酸金属盐、纤维素粉末、糊精、甲基丙烯酸酯的共聚物、聚乙烯吡咯烷酮、聚氨基羧酸螯合物、磺化苯乙烯·异丁烯·马来酸酐共聚物、淀粉·聚丙烯腈接枝共聚物等。
作为分解抑制剂,例如可举出:沸石、生石灰、氧化镁这样的干燥剂、酚化合物、胺化合物、硫化物、磷酸化合物等抗氧化剂、水杨酸化合物、二苯甲酮化合物等紫外线吸收剂等。
作为防腐剂,例如可举出山梨酸钾、1,2-苯并噻唑啉-3-酮等。此外,还可根据需要使用功能性铺展剂、增效醚等代谢分解抑制剂等活性增强剂、丙二醇等防冻剂、BHT等抗氧化剂、紫外线吸收剂等其它辅助剂。
有效成分化合物的混合比例可根据需要进行增减,在本发明的用于农业园艺的杀虫杀螨剂100重量份中,从0.01~90重量份的范围内适宜选择并使用即可,例如,在粉剂、粒剂、乳剂或可湿性粉剂的情况下,0.01~50重量份(相对于用于农业园艺的杀虫杀螨剂的总重量为0.01~50重量%)是适当的。
本发明的用于农业园艺的杀虫杀螨剂的使用量根据各种因素而变动,例如目的、目标害虫、作物的发育情况、害虫的发生倾向、天气、环境条件、剂型、施用方法、施用位置、施用时期等,作为有效成分化合物,根据目的从每10公亩0.001g~10kg,优选为0.01g~1kg的范围内适宜选择即可。
为了扩大防治对象病害虫、延长最佳防治时间或降低药量,可将本发明的用于农业园艺的杀虫杀螨剂与其他用于农业园艺的杀虫杀螨剂、杀螨剂、杀线虫剂、灭菌剂、生物农药等混合而进行使用,并且,还可根据使用情况与除草剂、植物生长调节剂、肥料等混合而进行使用。
作为用于该目的的其他农业园艺用杀虫剂、杀螨剂、杀线虫剂,例如可举出:3,5-二甲苯基甲基氨基甲酸酯(3,5-xylyl methylcarbamate,XMC)、仲丁威(fenobucarb,BPMC)、Bt毒素类杀虫性化合物、杀螨酯(chlorfenson,CPCBS)、二氯二异丙醚(dichlorodiisopropyl ether,DCIP)、1,3-二氯丙烯(1,3-Dichloropropene,D-D)、DDT、NAC、伐灭磷(O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate,DSP)、苯硫磷(O-ethyl O-4-nitrophenyl phenylphosphonothioate,EPN)、异氰尿酸三丙酯(tripropylisocyanurate,TPIC)、氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、acynonapyr、保棉磷(azinphos-methyl)、灭螨醌(acequinocyl)、啶虫脒(acetamiprid)、乙酰虫腈(acetoprole)、乙酰甲胺磷(acephate)、阿巴美丁(abamectin)、双丙环虫酯(afidopyropen)、阿维菌素-B(avermectin-B)、磺胺螨酯(amidoflumet)、双甲脒(amitraz)、棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、艾氏剂(aldrin)、α-硫丹(alpha-endosulfan)、α-氯氰菊酯(alpha-cypermethrin)、丙硫多菌灵(albendazole)、烯丙菊酯(allethrin)、氯唑磷(isazofos)、艾沙米多福(isamidofos)、异美沙同磷(isoamidofos)、噁唑磷(isoxathion)、isocycloseram、异柳磷(isofenphos)、异丙威(isoprocarb:MIPC)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、epsilon-momfluorothrin、伊维菌素(ivermectin)、新烟磷(imicyafos)、吡虫啉(imidac1oprid)、炔咪菊酯(imiprothrin)、茚虫威(indoxacarb)、S-氰戊菊酯(esfenvalerate)、乙硫苯威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、乙螨唑(etoxazole)、醚菊酯(ethofenprox)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、埃玛菌素(emamectin)、埃玛菌素苯甲酸盐(emamectin-benzoate)、硫丹(endosulfan)、右旋烯炔菊酯(empenthrin)、oxazosulfyl、杀线威(oxamyl)、亚砜磷(oxydemeton-methyl)、异亚砜磷(oxydeprofos:ESP)、奥苯达唑(oxibendazole)、奥芬达唑(oxfendazole)、油酸钾(Potassium oleate)、油酸钠(sodium oleate)、硫线磷(cadusafos)、kappa-tefluthrin、kappa-bifenthrin、杀螟丹(cartap)、甲萘威(carbary1)、丁硫克百威(carbosulfan)、克百威(carbofuran)、γ-氯氟氰菊酯(gamma-cyhalothrin)、灭杀威(xylylcarb)、喹硫磷(quinalphos)、烯虫炔酯(kinoprene)、灭螨猛(chinomethionat)、除线威(cloethocarb)、噻虫胺(clothianidin)、四螨嗪(clofentezine)、环虫酰肼(chromafenozide)、氯虫苯甲酰胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、杀虫脒(chlordimeform)、氯丹(chlordane)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、溴虫腈(chlorphenapyr)、杀螨酯(chlorfenson)、毒虫畏(ch1orfenvinphos)、氟啶脲(chlorfluazuron)、乙酯杀螨醇(chlorobenzilate)、氯苯甲酸酯(chlorobenzoate)、右旋反式氯炔丙菊酯(chloroprallethrin)、开乐散(三氯杀螨醇:dicofol)、水杨硫磷(salithion)、氯氟氰虫酰胺(cyhalodiamide)、杀螟腈(cyanophos:CYAP)、丁醚脲(diafenthiuron)、除线特(diamidafos)、溴氰虫酰胺(cyantraniliprole)、θ-氯氰菊酯(theta-cypermethrin)、遍地克(dienochlor)、腈吡螨酯(cyenopyrafen)、蔬果磷(dioxabenzofos)、苯虫醚(diofenolan)、σ-氯氰菊酯(sigma-cypermethrin)、环溴虫酰胺(cyclaniliprole)、除线磷(dichlofenthion:ECP)、乙氰菊酯(cycloprothrin)、敌敌畏(dichlorvos:DDVP)、二氯噻吡嘧啶(dicloromezotiaz)、乙拌磷(disulfoton)、呋虫胺(dinotefuran)、氯氟氰虫酰胺(cyhalodiamide)、氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氟氯氰菊酯(cyfluthrin)、除虫脲(diflubenzuron)、丁氟螨酯(cyflumetofen)、氟螨嗪(diflovidazin)、三环锡(cyhexatin)、氯氰菊酯(cypermethrin)、甲基毒虫畏(dimethylvinphos)、乐果(dimethoate)、嗪虫唑酰胺(dimpropyridaz)、四氟甲醚菊酯(dimefluthrin)、氟硅菊酯(silafluofen)、灭蝇胺(cyromazine)、乙基多杀菌素(spinetoram)、多杀霉素(spinosad)、螺螨酯(spirodiclofen)、螺虫乙酯(spirotetramat)、甲氧哌啶乙酯(spiropidion)、螺甲螨酯(spiromesifen)、氟虫胺(sulfluramid)、硫丙磷(sulprofos)、氟啶虫胺腈(sulfoxaflor)、ζ-氯氰菊酯(zeta-cypermethrin)、二嗪磷(diazinon)、氟胺氰菊酯(tau-fluvalinate)、棉隆(dazomet)、噻虫啉(thiacloprid)、tiaxazafen、噻虫嗪(thiamethoxam)、tioxazafen、硫双威(thiodicarb)、杀虫环(thiocyclam)、杀虫单(thiosultap)、杀虫双(thiosultap-sodium)、虫线磷(thionazin)、甲基乙拌磷(thiometon)、避蚊胺(deet)、狄氏剂(dieldrin)、四氯虫酰胺(Tetrachlorantraniliprole)、tyclopyrazoflor、杀虫畏(tetrach1orvinphos)、三氯杀螨砜(tetradifon)、四唑虫酰胺(tetraniliprole)、四氟醚菊酯(tetramethylfluthrin)、胺菊酯(tetramethrin)、丁基嘧啶磷(tebupirimfos)、虫酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、七氟菊酯(tefluthrin)、氟苯脲(teflubenzuron)、甲基内吸磷(demeton-S-methyl)、双硫磷(temephos)、溴氰菊酯(deltamethrin)、特丁硫磷(terbufos)、多拉菌素(Doramectin)、溴代吡咯腈(tralopyril)、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、唑蚜威(triazamate)、唑呀威(triazuron)、水杨菌胺(trichlamide)、敌百虫(trichlorphon:DEP)、三氟苯嘧啶(triflumezopyrium)、杀铃脲(triflumuron)、唑虫酰胺(tolfenpyrad)、二溴磷(naled:BRP)、硝虫噻嗪(nithiazine)、烯啶虫胺(nitenpyram)、氟酰脲(novaluron)、多氟脲(noviflumuron)、烯虫乙酯(hydroprene)、甲烯氟虫腈(vaniliprole)、蚜灭磷(vamidothion)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、苄螨醚(halfenprox)、氯虫酰肼(halofenozide)、双三氟虫脲(bistrifluron)、杀虫双(bisultap)、氟蚁腙(hydramethylnon)、羟丙基淀粉(hydroxypropyl starch)、乐杀螨(binapacryl)、pyflubumide、联苯肼酯(bifenazate)、联苯菊酯(bifenthrin)、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclorfos)、吡嗪氟虫腈(pyrafluprole)、哒嗪硫磷(pyridafenthion)、哒螨灵(pyridaben)、啶虫丙醚(pyridalyl)、氟虫吡喹(pyrifluquinazon)、吡啶氟虫腈(pyriprole)、吡丙醚(pyriproxyfen)、抗蚜威(pirimicarb)、嘧螨醚(pyrimidifen)、嘧螨胺(pyriminostrobin)、甲基嘧啶磷(pirimiphos-methyl)、除虫菊素(pyrethrins)、氟虫腈(fipronil)、喹螨醚(fenazaquin)、苯线磷(fenamiphos)、溴螨酯(bromopropylate)、杀螟硫磷(fenitrothion:MEP)、苯氧威(fenoxycarb)、苯硫威(fenothiocarb)、苯醚菊酯(phenothrin)、仲丁威(fenobucarb)、丰索磷(fensulfothion)、倍硫磷(fenthion:MPP)、稻丰散(phenthoate:PAP)、氰戊菊酯(fenvalerate)、唑螨酯(fenpyroximate)、甲氰菊酯(fenpropathrin)、芬苯达唑(fenbendazole)、噻唑磷(fosthiazate)、伐虫脒(formetanate)、特嘧硫磷(butathiofos)、噻嗪酮(buprofezin)、呋线威(furathiocarb)、右旋炔丙菊酯(prallethrin)、嘧螨酯(fluacrypyrim)、三氟咪啶酰胺(fluazaindolizine)、氟啶胺(fluazinam)、啶蜱脲(fluazuron)、氟噻虫砜(fluensulfone)、fluxametamide、氟环脲(flucycloxuron)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(fluvalinate)、氟吡呋喃酮(flupyradifurone)、丁烯氟虫腈(flufiprole)、吡氟硫磷(flupyrazofos)、flupyrimin、嘧虫胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、氟虫脲(flufenoxuron)、氟螨嗪(flufenzine)、三氟醚菊酯(flufenoprox)、苄螨醚(fluproxyfen)、溴氟菊酯(flubrocythrinate)、fluhexafon、氟虫酰胺(flubendiamide)、氟氯苯菊酯(flumethrin)、嘧虫胺(flurimfen)、丙硫磷(prothiofos)、普垂菊酯(protrifenbute)、氟啶虫酰胺(flonicamid)、丙虫磷(propaphos)、炔螨特(propargite:BPPS)、丙溴磷(profenofos)、溴虫氟苯双酰胺(broflanilide)、丙氟菊酯(profluthrin)、残杀威(propoxur:PHC)、flometoquin、alpha-bromadiolone、溴螨酯(bromopropylate)、β-氟氯氰菊酯(beta-cyfluthrin)、氟铃脲(hexaflumuron)、噻螨酮(hexythiazox)、右旋七氟甲醚菊酯(heptafluthrin)、庚烯磷(heptenophos)、氯菊酯(permethrin)、异噻虫唑(benclothiaz)、噁虫威(bendiocarb)、benzpyrimoxan、杀虫磺(bensu1tap)、苯螨特(benzoximate)、丙硫克百威(benfuracarb)、辛硫磷(phoxim)、伏杀硫磷(phosalone)、噻唑磷(fosthiazate)、丁硫环磷(fosthietan)、磷胺(phosphamidon)、磷虫威(phosphocarb)、亚胺硫磷(phosmet:PMP)、浏阳霉素复合物(polynactins)、伐虫脒(formetanate)、安硫磷(formothion)、甲拌磷(phorate)、机油(machine oil)、马拉硫磷(malathion)、米尔倍霉素(milbemycin)、米尔倍霉素A(milbemycin-A)、弥拜菌素(milbemectin)、灭蚜磷(mecarbam)、甲亚砜磷(mesulfenfos)、灭多威(methomyl)、四聚乙醛(metaldehyde)、氰氟虫腙(metaflumizone)、甲胺磷(methamidophos)、安百亩(metam-ammonium)、威百亩(metam-sodium)、甲硫威(methiocarb)、杀扑磷(methidathion:DMTP)、敌线酯(methylisothiocyanate)、甲基新癸酰胺(methylneodecanamide)、甲基对硫磷(methylparathion)、噁虫酮(metoxadiazone)、甲氧滴滴涕(methoxychlor)、甲氧虫酰肼(methoxyfenozide)、甲氧苄氟菊酯(metofluthrin)、烯虫酯(methoprene)、速灭威(metolcarb)、氯氟醚菊酯(meperfluthrin)、速灭磷(mevinphos)、久效磷(monocrotophos)、杀虫单(monosultap)、momfluorothrin、λ-氯氟氰菊酯(lambda-cyhalothrin)、鱼尼汀(ryanodine)、虱螨脲(lufenuron)、rescalure、苄呋菊酯(resmethrin)、雷皮菌素(lepimectin)、鱼藤酮(rotenone)、盐酸左旋咪唑(levamisol hydrochloride)、苯丁锡(fenbutatin oxide)、酒石酸甲噻嘧啶(morantel tartarate)、溴甲烷(methyl bromide)、三环锡(cyhexatin)、氰氨化钙(calcium cyanamide)、石硫合剂(calcium polysulfide)、硫(sulfur)和硫酸烟碱(nicotine-sulfate)、以及它们的盐。
作为以同样的目的使用的用于农业园艺的杀菌剂,例如可举出:金色制霉素(aureofungin)、阿扎康唑(azaconazole)、氧化福美双(azithiram)、培塔酸(acypetacs)、活化酯(acibenzolar)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敌菌灵(anilazine)、吲唑磺菌胺(amisulbrom)、aminopyrifen、氨丙磷酸(ampropylfos)、唑嘧菌胺(ametoctradin)、烯丙醇(allyl alcohol)、4-十二烷基-2,6-二甲基吗啉(aldimorph)、代森铵(amobam)、异噻菌胺(isotianil)、氯苯咪菌酮(isovaledione)、吡唑萘菌胺(isopyrazam)、异丙噻菌胺(isofetamid)、isoflucypram、稻瘟灵(isoprothiolane)、种菌唑(ipconazole)、ipfentrifluconazole、ipflufenoquin、异菌脲(iprodione)、缬霉威(iprovalicarb)、异稻瘟净(iprobenfos)、抑霉唑(imazalil)、双胍辛胺(iminoctadine)、威百亩(metam)、双胍三辛烷基苯磺酸盐(iminoctadine-albesilate)、双胍辛胺乙酸盐(iminoctadine-triacetate)、亚胺唑(imibenconazole)、inpyrfluxam、烯效唑(uniconazole)、烯效唑-P(uniconazole-P)、氯唑灵(echlomezole)、敌瘟磷(edifenphos)、乙环唑(etaconazole)、噻唑菌胺(ethaboxam)、乙嘧酚(ethirimol)、代森硫(etem)、乙氧喹啉(ethoxyquin)、土菌灵(etridiazole)、烯肟菌酯(enestroburin)、烯肟菌酯(enoxastrobin)、氟环唑(epoxiconazole)、噁霜灵(oxadixyl)、氟噻唑吡乙酮(oxathiapiprolin)、氧化萎锈灵(oxycarboxin)、8-羟基喹啉铜(copper-8-quinolinolate)、土霉素(oxytetracycline)、8-羟基喹啉铜(copper-oxinate)、噁咪唑(oxpoconazole)、噁咪唑富马酸盐(oxpoconazole-fumarate)、喹菌酮(oxolinic acid)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、威百亩(metam-sodium)、春雷霉素(kasugamycin)、吗菌威(carbamorph)、环丙酰菌胺(carpropamid)、多菌灵(carbendazim)、萎锈灵(carboxin)、香芹酮(carvone)、醌菌腙(quinazamid)、羟基喹啉基乙酮(quinacetol)、苯氧喹啉(quinoxyfen)、quinofumelin、灭螨猛(chinomethionat)、灭螨猛(quinomethionate)、敌菌丹(captafol)、克菌丹(captan)、精苯霜灵(kiralaxyl)、唑喹菌酮(quinconazole)、五氯硝基苯(quintozene)、双胍辛乙酸盐(guazatine)、硫杂灵(cufraneb)、福美铜氯(cuprobam)、丁香菌酯(coumoxystrobin)、果绿啶(glyodin)、灰黄霉素(griseofulvin)、咪菌酮(climbazole)、甲酚(cresol)、醚菌酯(kresoxim-methyl)、乙菌利(chlozolinate)、克霉唑(clotrimazole)、灭瘟唑(chlobenthiazone)、双胺灵(chloraniformethan)、四氯对醌(chloranil)、四氯喹喔啉(chlorquinox)、氯化苦(chloropicrin)、氯芬唑(chlorfenazole)、氯硝萘(chlorodinitrona phthalene)、百菌清(chlorothalonil)、地茂散(chloroneb)、水杨酰苯胺(salicylanilide)、氰菌胺(zarilamid)、氰霜唑(cyazofamid)、焦碳酸二乙酯(diethyl pyrocarbonate)、乙霉威(diethofencarb)、环菌胺(cyclafuramid)、双氯氰菌胺(diclocymet)、菌核利(dichlozoline)、苄氯三唑醇(diclobutrazol)、苯氟磺胺(dichlofluanid)、放线菌酮(cycloheximide)、dichlobentiazox、哒菌酮(diclomezine)、氯硝胺(dicloran)、双氯酚(dichlorophen)、二氯萘醌(dichlone)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、烯唑醇(diniconazole)、R-烯唑醇(diniconazole-M)、代森锌(zineb)、二硝巴豆酸酯(dinocap)、二硝酯(dinocton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、消螨通(dinobuton)、消戊酯(dinopenton)、dipymetitrone、双吡硫翁(dipyrithione)、二苯胺(diphenylamine)、苯醚甲环唑(difenoconazole)、环氟苄酰胺(cyflufenamid)、氟嘧菌胺(diflumetorim)、环菌唑(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、氰菌灵(cypendazole)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、烯酰吗啉(dimethomorph)、霜脲氰(cymoxanil)、醚菌胺(dimoxystrobin)、福美辛(ziram)、硅噻菌胺(silthiofam)、链霉素(streptomycin)、螺环菌胺(spiroxamine)、戊苯砜(sultropen)、氟唑环菌胺(sedaxane)、苯酰菌胺(zoxamide)、棉隆(dazomet)、代森环(thiadiazin)、噻酰菌胺(tiadinil)、噻二氟(thiadifluor)、噻菌灵(thiabendazole)、硫氰苯甲酰胺(tioxymid)、克杀螨(thioquinox)、硫氯苯亚胺(thiochlorfenphim)、硫菌灵(thiophanate)、甲基硫菌灵(thiophanate-methyl)、噻呋酰胺(thifluzamide)、噻菌腈(thicyofen)、克杀螨(thioquinox)、福美双(thiram)、癸磷锡(decafentin)、四氯硝基苯(tecnazene)、叶枯酞(tecloftalam)、福美双联(tecoram)、四氟醚唑(tetraconazole)、咪菌威(debacarb)、脱氢乙酸(dehydroacetic acid)、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、多地辛(dodicin)、多果定(dodine)、十二烷基苯磺酸双乙二胺铜盐(II)(DBEDC)、十二环吗啉(dodemorph)、肼菌酮(drazoxolon)、三唑醇(triadimenol)、三唑酮(triadimefon)、叶锈特(triazbutil)、咪唑嗪(triazoxide)、威菌磷(triamiphos)、嘧菌醇(triarimol)、水杨菌胺(trichlamide)、氯啶菌酯(triclopyricarb)、三环唑(tricyclazole)、灭菌唑(triticonazole)、十三吗啉(tridemorph)、三丁基氧化锡(tributyltin oxide)、氟菌唑(triflumizole)、肟菌酯(trifloxystrobin)、嗪氨灵(triforine)、甲苯氟磺胺(tolylfluanid)、甲基立枯磷(tolclofos-methyl)、tolprocarb、纳他霉素(natamycin)、代森钠(nabam)、硫氰散(nitrostyrene)、酞菌酯(nitrothal-isopropyl)、氟苯嘧啶醇(nuarimol)、壬基苯酚磺酸铜(coppernonylphenol sulfonate)、丙烯酸喹啉酯(halacrinate)、井冈霉素(validamycin)、霜霉灭(valifenalate)、超敏蛋白(harpin protein)、四唑吡氨酯(picarbutrazox)、联苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、氟吡菌胺(picobenzamide)、氟唑菌酰羟胺(pydiflumetofen)、硫氯酚(bithionol)、联苯三唑醇(bitertanol)、土菌消(hydroxyisoxazole)、土菌消钾(hydroisoxazole-potassium)、乐杀螨(binapacryl)、联苯(biphenyl)、病花灵(piperalin)、噁霉灵(hymexazol)、唑菌酯(pyraoxystrobin)、吡喃灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、联苯吡嗪菌胺(pyraziflumid)、吡菌磷(pyrazophos)、pyrapropoyne、唑胺菌酯(pyrametostrobin)、氯芬丽(pyriofenone)、啶菌腈(pyridinitril)、啶斑肟(pyrifenox)、啶菌噁唑(pyrisoxazole)、pyridachlometyl、啶斑肟(pyrifenox)、吡菌苯威(pyribencarb)、嘧螨胺(pyriminostrobin)、嘧霉胺(pyrimethanil)、氯甲氧吡啶(pyroxychlor)、氯吡呋醚(pyroxyfur)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、福美铁(ferbam)、噁唑菌酮(famoxadone)、咪菌腈(fenapanil)、咪唑菌酮(fenamidone)、敌磺钠(fenaminosulf)、烯肟菌胺(fenaminstrobin)、氯苯嘧啶醇(fenarimol)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、嘧菌腙(ferimzone)、福美铁(ferbam)、三苯锡(fentin)、拌种咯(fenpiclonil)、fenpicoxamid、胺苯吡菌酮(fenpyrazamine)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、环酰菌胺(fenhexamid)、四氯苯酞(phthalide)、丁硫啶(buthiobate)、丁胺(butylamine)、乙嘧酚磺酸酯(bupirimate)、麦穗宁(fuberidazole)、灭瘟素(blasticidin-S)、呋吡菌胺(furametpyr)、呋霜灵(furalaxyl)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、氟茚唑菌胺(fluindapyr)、氟嘧菌酯(fluoxastrobin)、fluoxapiprolin、三氟苯唑(fluotrimazole)、氟吡菌胺(fluopicolide)、Fluopimomide、氟吡菌酰胺(fluopyram)、氟氯菌核利(fluoroimide)、二甲呋酰胺(furcarbanil)、氟唑菌酰胺(fluxapyroxad)、氟喹唑(fluquinconazole)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、咯菌腈(fludioxonil)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟噻菌净(flutianil)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、氟菌螨酯(flufenoxystrobin)、糠醛(furfural)、拌种胺(furmecyclox)、氟酰菌胺(flumetover)、氟吗啉(flumorph)、丙氧喹啉(proquinazid)、咪鲜胺(prochloraz)、腐霉利(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、pronitridine、霜霉威(propamocarb)、丙环唑(propiconazole)、丙森锌(propineb)、呋甲硫菌灵(furophanate)、烯丙苯噻唑(probenazole)、糠菌唑(bromuconazole)、florylpicoxamid、六氯丁二烯(hexachlorobutadiene)、己唑醇(hexaconazole)、环己硫磷(hexylthiofos)、吡托沙嗪(bethoxazin)、苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、稻瘟酯(pefurazoate)、醌肟腙(benquinox)、戊菌唑(penconazole)、苯杂吗(benzamorf)、戊菌隆(pencycuron)、苯甲羟肟酸(benzohydroxamic acid)、苯并烯氟菌唑(benzovindiflupyr)、丙唑草隆(bentaluron)、苯噻硫氰(benthiazole)、benthiavalicarb、苯噻菌胺异丙酯(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、氟唑菌苯胺(penflufen)、烟酰胺(boscalid)、氯瘟磷(phosdiphen)、三乙膦酸(fosetyl)、三乙膦酸铝(fosetyl-Al)、多氧霉素(polyoxins)、多抗霉素(polyoxorim)、代森福美锌(polycarbamate)、灭菌丹(folpet)、甲醛(formaldehyde)、机油(machine oil)、代森锰(maneb)、代森锰锌(mancozeb)、双炔酰菌胺(mandipropamid)、mandestrobin、甲菌利(myclozolin)、腈菌唑(myclobutanil)、米多霉素(mildiomycin)、代森环(milneb)、苯并威(mecarbinzid)、磺菌威(methasulfocarb)、间氯敌菌酮(metazoxolon)、威百亩(metam)、威百亩钠盐(metam-sodium)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、代森联(metiram)、异硫氰酸甲酯(methyl isothiocyanate)、敌螨普(mepthyldinocap)、metyltetraprole、叶菌唑(metconazole)、噻菌胺(metsulfovax)、呋菌胺(methfuroxam)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、嘧菌胺(mepanipyrim)、精甲霜灵(mefenoxam)、氯氟醚菌唑(mefentrifluconazole)、消螨多(meptyldinocap)、灭锈胺(mepronil)、邻酰胺(mebenil)、碘甲烷(iodomethane)、吡咪唑(rabenzazole)、溴甲烷(methyl bromide)、苯扎氯铵(benzalkonium chloride)、碱式氯化铜(basic copperchloride)、碱式硫酸铜(basic copper sulfate)、金属银(silver)等无机灭菌剂、次氯酸钠(sodium hypochlorote)、氢氧化铜(cupric hydroxide)、水和硫剂(wettable sulfur)、石硫合剂(calcium polysulfide)、碳酸氢钾(potassium hydrogen carbonate)、碳酸氢钠(sodium hydrogen carbonate)、无机硫(sulfur)、无水硫酸铜(copper sulfateanhydride)、二甲氨基二硫代甲酸镍(nickel dimethyldithiocarbamate)、8-羟基喹啉铜(oxine copper)这样的铜类化合物、硫酸锌(zinc sulfate)和五水硫酸铜(coppersulfate pentahydrate)、以及它们的盐。
同样,作为除草剂,例如可举出:1-萘乙酰胺、2,4-PA、2,3,6-TBA、2,4,5-T、2,4,5-TB、2,4-D、2,4-DB、2,4-DEB、2,4-DEP、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、MCP、MCPA、MCPA乙硫酯、MCPB、碘苯腈(ioxynil)、苯草醚(aclonifen)、唑啶草酮(azafenidin)、三氟羧草醚(acifiuorfen)、叠氮津(aziprotryne)、四唑嘧磺隆(azimsulfuron)、磺草灵(asulam)、乙草胺(acetochlor)、莠去津(atrazine)、莠去通(atraton)、疏草隆(anisuron)、莎稗磷(anilofos)、四烯雌酮(aviglycine)、脱落酸(abscisic acid)、氨唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、杀草强(amitrole)、环丙吡啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、特草嗪酮(amibuzin)、甲基胺草磷(amiprophos-methyl)、特津酮(ametridione)、莠灭净(ametryn)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、五氯戊酮酸(alorac)、iofensulfuron、异噁隆(isouron)、丁咪酰胺(isocarbamid)、异噁氯草酮(isoxachlortole)、异噁草醚(isoxapyrifop)、异噁唑草酮(isoxaflutole)、异噁酰草胺(isoxaben)、异草定(isocil)、异草完隆(isonoruron)、异丙隆(isoproturon)、异丙乐灵(isopropalin)、氮萆草(isopolinate)、丁嗪草酮(isomethiozin)、抗倒胺(inabenfide)、抑草津(ipazine)、三唑酸草胺(ipfencarbazone)、丙草定(iprymidam)、灭草喹(imazaquin)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、甲基咪草烟(imazamethapyr)、咪草酸(imazamethabenz)、咪草甲酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、咪草烟(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、三嗪茚草胺(indaziflam)、茚草酮(indanofan)、吲哚丁酸(indolebutyric acid)、烯效唑-P(uniconazole-P)、甘草津(eglinazine)、戊草丹(esprocarb)、胺苯磺隆(ethametsulfuron)、胺苯磺隆甲酯(ethametsulfuron-methyl)、乙丁烯氟灵(ethalfluralin)、硫草敌(ethiolate)、吲熟酯(ethychlozate ethyl)、磺噻隆(ethidimuron)、硝草酚(etinofen)、乙烯利(ethephon)、乙氧磺隆(ethoxysulfuron)、氯氟草醚(ethoxyfen)、乙胺草醚(etnipromid)、乙氧呋草黄(ethofumesate)、乙氧苯草胺(etobenzanid)、三唑磺(epronaz)、抑草蓬(erbon)、草藻灭(endothal)、噁草酮(oxadiazon)、丙炔噁草酮(oxadiargyl)、噁嗪草酮(oxaziclomefone)、环氧嘧磺隆(oxasulfuron)、草哒松(oxapyrazon)、乙氧氟草醚(oxyfluorfen)、氨磺乐灵(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、唑草胺(cafenstrole)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、唑草酮(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、特胺灵(karbutilate)、草长灭(carbetamide)、特噁唑威(carboxazole)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、喹禾灵乙酯(quizalofop-ethyl)、二甲苯草胺(xylachlor)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、苄草隆(cumyluron)、氯酰草膦(clacyfos)、碘氯啶酯(cliodinate)、草甘膦(glyphosate)、草铵膦(glufosinate)、精草铵膦(glufosinate-P)、醚草敏(credazine)、烯草酮(clethodim)、座果酸(cloxyfonac)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、绿麦隆(chlorotoluron)、二氯吡啶酸(clopyralid)、环丁烯草酮(cloproxydim)、调果酸(cloprop)、氯溴隆(chlorbromuron)、氯丁草(clofop)、异噁草松(clomazone)、氯硝醚(chlomethoxynil)、甲氧除草醚(chlomethoxyfen)、氯甲酰草胺(clomeprop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯酯磺草胺(cloransulam)、丁酰草胺(chloranocryl)、草灭畏(chloramben)、cloransulam、氯酯磺草胺(cloransulam-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆乙酯(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、敌草索(chlorthal)、氯硫酰草胺(chlorthiamid)、绿麦隆(chlortoluron)、草枯醚(chlornitrofen)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氯炔灵(chlorbufam)、氯酰亚胺(chlorphthalim)、氟咪杀(chlorflurazole)、氯甲丹(chlorflurenol)、草败死(chlorprocarb)、氯苯胺灵(chlorpropham)、矮壮素(chlormequat)、乙氧苯隆(chloreturon)、羟敌草腈(chloroxynil)、枯草隆(chloroxuron)、绿麦隆(chlorotoluron)、三氯丙酸(chloropon)、苯嘧磺草胺(saflufenacil)、氰草津(cyanazine)、氰草净(cyanatryn)、燕麦敌(di-allate)、敌草隆(diuron)、二乙除草双(diethamquat)、麦草畏(dicamba)、环莠隆(cycluron)、环草敌(cycloate)、噻草酮(cycloxydim)、双氯磺草胺(diclosulam)、环丙嘧磺隆(cyclosulfamuron)、cyclopyranil、cyclopyrimorate、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、敌草腈(dichlobenil)、禾草灵(diclofop)、禾草灵甲酯(diclofop-methyl)、苄胺灵(dichlormate)、氯全隆(dichloralurea)、敌草快(diquat)、咯草隆(cisanilide)、2,4-滴硫钠(disul)、环草隆(siduron)、氟硫草定(dithiopyr)、氨氟灵(dinitramine)、吲哚酮草酯(cinidon-ethyl)、戊硝酚(dinosam)、醚磺隆(cinosulfuron)、地乐酚(dinoseb)、特乐酚(dinoterb)、地乐特(dinofenate)、硝丙酚(dinoprop)、氰氟草酯(cyhalofop-butyl)、双苯酰草胺(diphenamid)、枯莠隆(difenoxuron)、戊味禾草灵(difenopenten)、野燕枯(difenzoquat)、洒布净(cybutryne)、环丙津(cyprazine)、三环赛草胺(cyprazole)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、异丙净(dipropetryn)、环酰草胺(cypromid)、牧草快(cyperquat)、赤霉素(gibberellin)、西玛津(simazine)、草灭散(dimexano)、二甲草胺(dimethachlor)、草哒酮(dimidazon)、异戊津(dimethametryn)、二甲吩草胺(dimethenamid)、西草净(simetryn)、西玛通(simeton)、哌草丹(dimepiperate)、噁隆(dimefuron)、环庚草醚(cinmethylin)、灭草灵(swep)、吖庚磺酯(sulglycapin)、磺草酮(sulcotrione)、菜草畏(sulfallate)、甲磺草胺(sulfentrazone)、磺酰磺隆(sulfosulfuron)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、仲丁通(secbumeton)、稀禾定(sethoxydim)、另丁津(sebuthylazine)、特草定(terbacil)、杀草隆(daimuron)、棉隆(dazomet)、茅草枯(dalapon)、噻氟隆(thiazafluron)、噻草定(thiazopyr)、氟嘧硫草酯(tiafenacil)、噻酮磺隆(thiencarbazone)、噻酮磺隆甲酯(thiencarbazone-methyl)、仲草丹(tiocarbazil)、嘧草胺(tioclorim)、禾草丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、甜菜安(desmedipham)、敌草净(desmetryn)、tetflupyrolimet、四氟隆(tetrafluron)、噻吩草胺(thenylchlor)、牧草胺(tebutam)、丁噻隆(tebuthiuron)、特丁通(terbumeton)、吡喃草酮(tepraloxydim)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、异丁草胺(delachlor)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁津(terbuthylazine)、特丁净(terbutryn)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、三嗪氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、草达津(trietazine)、杀草畏(tricamba)、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、三氟草嗪(trifludimoxazin)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、茚草酮(tripropindan)、苯磺隆(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三甲隆(trimeturon)、tolpyralate、萘草胺(naptalam)、萘丙胺(naproanilide)、敌草胺(napropamide)、烟嘧磺隆(nicosulfuron)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、氟氯草胺(nipyraclofen)、草不隆(neburon)、哒草伏(norflurazon)、草完隆(noruron)、燕麦灵(barban)、多效唑(paclobutrazol)、百草枯(paraquat)、对氟隆(parafluron)、氟啶草(haloxydine)、氟氯吡啶酸(halauxifen)、氟吡禾灵(haloxyfop)、高效氟吡甲禾灵(haloxyfop-P)、氟吡甲禾灵(haloxyfop-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯(halosulfuron-methyl)、双丙氨酰膦(bilanafos)、二氯异噁草酮(bixlozone)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、氟吡草酮(bicyclopyrone)、双草醚(bispyribac)、双草醚钠盐(bispyribac-sodium)、比达农(pydanon)、唑啉草酯(pinoxaden)、甲酸除草醚(bifenox)、哌草磷(piperophos)、噁霉灵(hymexazol)、双唑草腈(pyraclonil)、磺酰草吡唑(pyrasulfotole)、苄草唑(pyrazoxyfen)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯(pyrazosulfuron-ethyl)、吡唑特(pyrazolate)、双丙氨酰膦(bilanafos)、吡草醚(pyraflufen-ethyl)、三氯吡啶酚(pyriclor)、哒草醇(pyridafol)、嘧草硫醚(pyrithiobac)、嘧草硫醚钠盐(pyrithiobac-sodium)、哒草特(pyridate)、环酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧磺苯胺(pyrimisulfan)、氟嘧磺隆(primisulfuron)、嘧草醚(pyriminobac-methyl)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、酰苯磺威(fenasulam)、棉胺宁(phenisopham)、非草隆(fenuron)、异噁苯砜(fenoxasulfone)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵乙酯(fenoxaprop-ethy1)、酚硫杀(phenothiol)、2,4,5-涕丙酸(fenoprop)、酰草隆(phenobenzuron)、fenquinotrione、噻唑禾草灵(fenthiaprop)、氯苯氧乙醇(fenteracol)、四唑酰草胺(fentrazamide)、甜菜宁(phenmedipham)、甜菜宁乙酯(phenmedipham-ethyl)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁噻隆(buthiuron)、特咪唑草(buthidazole)、丁草敌(butylate)、炔草隆(buturon)、丁烯草胺(butenachlor)、丁苯草酮(butroxydim)、仲丁灵(butralin)、丁苯草酮(butroxydim)、啶嘧磺隆(flazasulfuron)、麦草氟(flamprop)、呋氧草醚(furyloxyfen)、丙炔草胺(prynachlor)、氟嘧磺隆甲酯(primisulfuron-methyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、异丙吡草酯(fluazolate)、氟草烟(fluroxypyr)、氟硫隆(fluothiuron)、氟草隆(fluometuron)、乙羧氟草醚(fluoroglycofen)、氟咯草酮(flurochloridone)、三氟硝草醚(fluorodifen)、氟除草醚(fluoronitrofen)、唑啶草(fluoromidine)、氟唑磺隆(flucarbazone)、氟唑磺隆钠盐(flucarbazone-sodium)、氯乙氟灵(fluchloralin)、氟吡磺隆(flucetosulfuron)、嗪草酸(fluthiacet)、嗪草酸甲酯(fiuthiacet-methyl)、氟啶嘧磺隆(flupyrsulfuron)、氟噻草胺(flufenacet)、氟苯啶草(flufenican)、氟哒嗪草酯(flufenpyr)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanate)、氟胺草唑(flupoxam)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac)、氟烯草酸戊酯(flumiclorac-pentyl)、炔草胺(flumipropyn)、三氟噁嗪(flumezin)、氟草隆(fluometuron)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氟草烟(fluroxypyr)、丙草胺(pretilachlor)、扑灭生(proxan)、甘扑津(proglinazine)、环丙腈津(procyazine)、氨氟乐灵(prodiamine)、甲硫磺乐灵(prosulfalin)、氟磺隆(prosulfuron)、苄草丹(prosulfocarb)、喔草酸(propaquizafop)、毒草胺(propachlor)、扑灭津(propazine)、敌稗(propanil)、炔苯酰甲胺(propyzamide)、异丙草胺(propisochlor)、茉莉酮(prohydrojasmon)、嗪咪唑嘧磺隆(propyrisulfuron)、苯胺灵(propham)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、调环酸钙(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠盐(propoxycarbazone-sodium)、环苯草酮(profoxydim)、除草定(bromacil)、溴草敏(brompyrazon)、扑草净(prometryn)、扑灭通(prometon)、溴苯腈(bromoxynil)、溴酚肟(bromofenoxim)、溴丁酰草胺(bromobutide)、糠草腈(bromobonil)、双氟磺草胺(florasulam)、florpyrauxifen、六氯丙酮(hexachloroacetone)、环嗪酮(hexazinone)、烯草胺(pethoxamid)、草除灵(benazolin)、五氟磺草胺(penoxsulam)、克草敌(pebulate)、氟丁酰草胺(beflubutamid)、beflubutamid-M、灭草敌(vernolate)、黄草伏(perfluidone)、苯唑磺隆(bencarbazone)、胺酸杀(benzadox)、苄草胺(benzipram)、苄基氨基嘌呤(benzylaminopurine)、苯噻隆(benzthiazuron)、双苯嘧草酮(benzfendizone)、地散磷(bensulide)、苄嘧磺隆甲酯(bensulfuron-methyl)、新燕灵(benzoylprop)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟草黄(benzofluor)、灭草松(bentazone)、甲氯酰草胺(pentanochlor)、禾草丹(benthiocarb)、二甲戊灵(pendimethalin)、环戊噁草酮(pentoxazone)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、蔓草磷(fosamine)、氟磺胺草醚(fomesafen)、甲酰氨基嘧磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、抑芽丹(maleic hydrazide)、2-甲-4-氯丙酸(mecoprop)、精-2-甲-4-氯丙酸(mecoprop-P)、地乐施(medinoterb)、甲基二磺隆(mesosulfuron)、甲基二磺隆甲酯(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、灭莠津(mesoprazine)、格草净(methoprotryne)、吡草胺(metazachlor)、灭草唑(methazole)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、苯嗪草酮(metamitron)、噁唑酰草胺(metamifop)、威百亩(metam)、氟烯硝草(methalpropalin)、灭草恒(methiuron)、异噁噻草醚(methiozolin)、甲硫苯威(methiobencarb)、甲基杀草隆(methyldymron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron)、甲磺隆甲酯(metsulfuron-methyl)、氟哒草(metflurazon)、溴谷隆(metobromuron)、吡喃隆(metobenzuron)、醚草通(methometon)、异丙甲草胺(metolachlor)、嗪草酮(metribuzin)、甲哌鎓(mepiquat-chloride)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、庚酰草胺(monalide)、特噁唑隆(monisouron)、灭草隆(monuron)、一氯乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、禾草敌(molinate)、伐草快(morfamquat)、碘磺隆(iodosulfuron)、碘磺隆甲酯钠盐(iodosulfuron-methyl-sodium)、碘草腈(iodobonil)、碘甲烷(iodomethane)、乳氟禾草灵(lactofen)、lancotrione、利谷隆(linuron)、砜嘧磺隆(rimsulfuron)、环草定(lenacil)、硫氰苯胺(rhodethanil)、过氧化钙(calcium peroxide)和溴甲烷(methyl bromide)、以及它们的盐。
同样,作为生物农药,例如可举出:放射形土壤杆菌(Agrobacteriumradiobacter)(例如,使用了株K84的“AgBioChem,CA”制的“Galltrol-A(注册商标)”、使用了株K1026的“Becker Underwood,US”制的“Nogall(注册商标)”)、放射形土壤杆菌(Agrobacterium radiobacter)(例如,使用了株84的“日本农药(株式会社)”制的“Bacterose(注册商标)”)、白粉寄生孢(Ampelomyces quisqualis)(例如,使用了株AQ10的“IntrachemBio Italia&Co.KG”制的“AQ 10(注册商标)”)、黄曲霉(Aspergillus flavus)(例如,“Syngenta”制的“Afla-Guard(注册商标)”、使用了株AF36的“Arizona CottonResearch and Protection Council,US”制的“AF36(注册商标)”、使用了NRRL 21882的“Syngenta”制的“Afla-Guard”)、出芽短梗霉(Aureobasidium pullulans)(例如,作为株DSM14940的出芽孢子和株DSM14941的出芽孢子的混合物的“bio-ferm,GmbH”制的“Botector(注册商标)”)、解淀粉芽孢杆菌(Bacillus amyloliquefaciens)(例如,使用了株AT-332的“IDEMITSU AGRI(株式会社)”制的“IMPRESSION CLEAR(注册商标)”、使用了株B246的“University of Pretoria”制的“Avogreen(注册商标)”、株D747(例如,“Etec CropSolutions,NZ”制的“Bacstar(注册商标)”、使用了株DB101的“Dagutat Bio lab,ZA”制的“Shelter(注册商标)”、使用了株DB102的“Dagutat Bio lab,ZA”制的“Artemis(注册商标)”、使用了株FZB42的“ABiTEP,DE”制的“RhizoVital(注册商标)”、使用了株GB03的“Bayer Crop Science AG,DE”制的“Kodiak(注册商标)”、使用了株MBI600的“BeckerUnderwood,US”制的“Subtilex(注册商标)”、使用了株F727的“Marrone Bio Innovations,Inc.”制的“Amplitude”)、Bacillus cepacia(例如,“Microbial Products”制的“DenyStine(注册商标)”)、蜡样芽孢杆菌(Bacillus cereus)(例如,使用了株BP01的“Arysta,US”制的“Mepichlor(注册商标)”)、坚强芽孢杆菌(Bacillus firmus)(例如,使用了株I-1582的“AgoGreen制)的“BioNeem(注册商标)”)、栖乳芽孢杆菌(Bacillus lacticola)(例如,“Micro Flo Company”制)、乳病杆菌(Bacillus lactimorbus)(例如,“Micro FloCompany”制)、乳杆菌(Bacillus lactis)(例如,“Micro Flo Company”制)、侧孢芽孢杆菌(Bacillus laterosporus)(例如,“Agro-Organics,SA”制的“Bio-Tode(注册商标)”)、地衣芽孢杆菌(Bacillus licheniformis)(例如,使用了株SB3086的“Novozymes”制的“EcoGuard Biofungicide(注册商标)”)、摩洛哥芽孢杆菌(Bacillus maroccanus)(例如,“Micro Flo Company”制)、巨大芽孢杆菌(Bacillus megaterium)(例如,使用了株YFM3.25的“Bio Arc”制的“Bioarc(注册商标)”)、Bacillus metiens(例如,“Micro Flo Company”制)、摩加夫芽孢杆菌(Bacillus mojavensis)(例如,使用了株SR11的“Probelte,Sa”制)、蕈状芽孢杆菌(Bacillus mycoides)(例如,使用了分离株J.的“Certis USA”制的“BmJ(注册商标)”)、枯草芽孢杆菌(Bacillus nigrificans)(例如,“Micro Flo Company”制)、日本金龟子芽孢杆菌(Bacillus popilliae)(例如,“Bio Crop,CO”制的“Cronox(注册商标)”)、短小芽孢杆菌(Bacillus pumilus)(例如,使用了株BU F-33的“Becker Underwood,US”制的“Integral F-33(注册商标)”、使用了株GB34的“Bayer Crop Science AG,DE”制的“Yield Shield(注册商标)”、使用了株QST2808的“Bayer CropScience LP,US”制的“Sonata(注册商标)”)、简单芽孢杆菌(Bacillus simplex)(例如,使用了株CGF2856的“Arysta Life Science(株式会社)”制的“Momihope Wettable Powder(注册商标)”)、球形芽孢杆菌(Bacillus sphaericus)(例如,使用了抗原型H5a5b株2362的“ValentBioSciences,US”制的“VectoLex(注册商标)”)、枯草芽孢杆菌(Bacillus subtilis)(例如“IDEMITSU AGRI(株式会社)”制的“Botokiller Wettable Powder(注册商标)”、使用了株FZB24的“Novozyme Biologicals,Inc.US”制的“Taegro(注册商标)”、使用了株QST713/AQ713的“Bayer CropScienceLP,US”制的“SERENADEMAX(注册商标)”、使用了株AQ30002的“Serenade-DPZ(注册商标)”、使用了株D747的“KUMIAI CHEMICAL INDUSTRY(株式会社)”制的“ECOSHOT(注册商标)”、使用了株HAI-0404的“(株式会社)NISSO GREEN”制的“AgrocareWettable Powder(注册商标)”,使用了株MBI600的“发光兴产(株式会社)”制的“BotopikaWettable Powder(注册商标)”、使用了株Y1336的“Arysta Life Science(株式会社)”制的“BaciStar Wettable Powder(注册商标)”、使用了株GB03的“Growth Products Ltd”制的“Companion Biological Fungicide Wettable Powder”)、苏云金杆菌(Bacillusthuringiensis)(例如,使用了株AM65-52的“Valent BioSciences,US”制的“VectoBac(注册商标)”)、Bacillus thuringienses aizawai(例如,使用了株ABTS-1857的“Bayer CropScience AG,DE”制的“XenTari(注册商标)”、使用了抗原型H-7的“Valent BioSciences,US”制的“Florbac WG(注册商标)”、使用了株GC-91的“Certis USA”制的“Agree WGBiological Insecticide”)、Bacillus thuringiensis subspecies.Aegypti(例如,“Agerin(注册商标)”)、苏芸金芽胞杆菌以色列亚种(Bacillus thuringiensesisraelensis)(例如,使用了株BMP144的“Becker Microbial Products IL”制的“Aquabac(注册商标)”)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringienses kurstaki)(例如,使用了株BMP 123的“Becker Microbial Products,IL”制、使用了株HD-1的“ValentBioSciences,US”制的“Dipel ES(注册商标)”、使用了株BMP123的“Becker MicrobialProducts”制的“BMP 123”、使用了株BMP144的“Becker Microbial Products”制的“BMP144/Aquabac”、使用了株ABTS-351的“Valent U.S.A.LLC.”制的“Dipel 10G”、使用了株EG2348的“Certis USA”制的“Condor Wettable Powder”、使用了株EG7841的“CertisUSA”制的“Crymax Bioinsecticide”、使用了株SA-12的“Certis USA”制的“DeliverBiological Insecticide”、使用了株EVB-113-19的“AEF Global”制的“BioprotecPLUS”)、苏云金杆菌蜡螟亚种(Bacillus thuringiensis galleriae)(例如,“PhyllomBioProducts”制的“beetleGONE!”、使用了株SDS-502的“Phyllom BioProducts”制的“boreGONE!”)、苏云金芽孢杆菌默尔变种(Bacillus thuringiensis var.Colmeri)(例如,“Changzhou Jianghai Chemical Factory”制的“TianBaoBTc(注册商标)”)、苏云金芽胞杆菌拟步行甲亚种(Bacillus thuringienses tenebrionis)(例如,使用了株NB 176的“BioFa DE”制的“Novodor FC(注册商标)”)、苏云金芽孢杆菌圣地亚哥变种(Bacillusthuringiensis var.san diego)(例如,“Bacillus thuringiensis var.san diego”制的“M-One(注册商标)”)、球孢白僵菌(Beauveria bassiana)(例如,“Intrachem Bio Italia”制的“Naturalis(注册商标)”、使用了株CG716的“Novozymes”制的“Bove Max(注册商标)”、使用了株F-263的“发光兴产(株式会社)”制的“Baiorisa madara(注册商标)”、使用了株GHA的“ARYSTA”制的“Botanigard Wettable Powder(注册商标)”、使用了株HF23的“Terragena,Inc.”制的“balEnce”、使用了株GHA的“BioWorks Inc.”制的“BotaniGardES”、使用了株ANT-03的“BioSafe Systems”制的“BioCeres WP”)、布氏白僵菌(Beauveriabrongniartii)(例如,“Andermatt Biocontrol AG”制的“Beaupro(注册商标)”)、大豆慢生根瘤菌(Bradyrhizobium japonicum)(例如,“Novozymes”制的“Optimize(注册商标)”)、伯克霍尔德菌(Burkholderia spp.)(例如,使用了株A396的“Marrone Bio Innovations”制的“MBI-206 TGAI(注册商标)”)、橄榄假丝酵母(Candida oleophila)(例如,使用了株I-82的“Ecogen Inc.,US”制的“Aspire(注册商标)”、使用了O株的“BioNext”制的“Nexy(注册商标)”)、水解假丝酵母(Candida saitoana)(例如“,Micro Flo Company,US(BASF SE)”制的“BIOCURE(注册商标)”)、角毛壳菌(Chaetomium cupreum)(例如,“AgriLife”制的“BIOKUPRUM TM(注册商标)”)、球毛壳菌(Chaetomium globosum)(例如,“Rivale”制的“Rivadiom(注册商标)”)、铁杉下色杆菌(Chromobacterium subtsugae)(例如,使用了株PRAA4-1T的“Marrone Bio Innovations”制的“Grandevo(注册商标)”)、枝孢样枝孢霉(Cladosporium cladosporioides)(例如,“Cladosporium cladosporioides”制)、链孢粘帚霉(Clonostachys rosea f.catenulate)(例如,使用了株J 1446的“Verdera,Finland”制的“PRESTOP(注册商标)”)、胶孢炭疽菌(Colletotrichum gloeosporioides)(例如,“Agriultural Research Initiatives”制的“Collego(注册商标)”)、盾壳霉菌(Coniothyrium minitans)(例如,使用了株CON/M/91-08的“Encore Technologies,LLC”制的“Contans(注册商标)”)、浅白隐球酵母(Cryptococcus albidus)(例如,“Anchor BioTechnologies,ZA”制的“YieldPlus(注册商标)”)、食酸戴尔福特菌(Delftiaacidovorans)(例如,使用了株RAY209的“Brett Young Seeds”制的“BioBoost(注册商标)”)、Dilophosphora alopecuri(例如,“Twist Fungus(注册商标)”)、Drechsrelamonoceras(例如,使用了株MTB-951的“MITSUI CHEMICALS AGRO(株式会社)”制的“Tasumato herbicide(注册商标)”)、毒力虫霉(Entomophthora virulenta)(例如,“Ecomic”制的“Vektor(注册商标)”)、尖孢镰刀菌(Fusarium oxysporum)(例如,使用了株101-2的“Eisai Seikaken公司”制的“Maruka light”)、尖孢镰刀菌(Fusarium oxysporum)(例如,使用了株Fo47的“Natural Plant Protection”制的“Fusaclean(注册商标)”)、粘帚霉(Gliocladium spp.)(例如,使用了株J1446的“AgBio Inc.”制的“Prestop(注册商标)”、使用了株321U的“W.F.Stoneman Company LLC”制)、汤氏多毛菌(Hirsutella thompsonii)(例如,“Agro Bio tech Research Centre,IN”制的“Mycohit(注册商标)”)、嗜酸乳杆菌(Lactobacillus acidophilus)(例如,“Inagrosa Industrias Agrobiologicas,S.A”制的“Fruitsan(注册商标)”)、植物乳杆菌(Lactobacillus plantarum)(例如,使用了株BY的“Meiji Seika Pharma(株式会社)”制的“Lactoguard Wettable Powder”)、蜡蚧轮枝菌(Lecanicillium lecanii)(例如,使用了株KV01的分生孢子的“Koppert/Arysta”制的“Mycotal(注册商标)”)、金龟子绿僵菌(Metarhizium anisopliae)(例如,使用了株F52的“Bayer CropScience”制的“BIO 1020(注册商标)”、使用了株SMZ-2000的“Arysta LifeScience(株式会社)”制的“Pirates G(注册商标)”、使用了株ESC1的“LidoChem Inc”制的“Bio-Blast”)、Metarhizium anisopliae var.acridum(例如,“Biological ControlProducts”制的“Green Muscle(注册商标)”、“Becker Underwood,US”制的“GreenGuard(注册商标)”)、核果梅奇酵母(Metschnikowia fructicola)(例如,“Bayer CropScience”制的“Shemer(注册商标)”)、Microdochium dimerum(例如,“Agrauxine,France”制的“ANTIBOT(注册商标)”)、Micro sphaeropsis ochracea(例如,“Prophyta”制的“Microx(注册商标)”)、瘤捕单顶孢(Monacrosporium phymatopagum)(例如,“Tomoe化学工业(株式会社)”制的“Nemahiton(注册商标)”)、冻土毛霉(Mucor haemelis)(例如,“Indore BiotechInputs&Research”制的“BioAvard(注册商标)”)、(Muscodor albus)(例如,使用了株QST20799的“Bayer Crop Science”制的“Arabesque”)、疣孢漆斑菌(Myrotheciumverrucaria)(例如,使用了株AARC-0255的“Valent Biosciences”制的“DiTeraTM(注册商标)”)、玫烟色拟青霉(Paecilomyces fumosoroseus)(例如,使用了株apopka 97的“Biobest”制的“PreFeRal(注册商标)WG”、“东海物产(株式会社)”制的“Prifado WettablePowder”、使用了株FE 9901的“Natural Industries Inc.(Novozymes company)”制的“NoFly(注册商标)”)、淡紫拟青霉(Paecilomyces lilacinus)(例如,使用了株251的“Prophyta”制的“BioAct WG(注册商标)”)、细脚拟青霉(Pacilimyces tenuipes)(例如,使用了株T1的“发光兴产(株式会社)”制的“Gottsu A(注册商标)”)、宛氏拟青霉(Paecilomyces variotii)(例如,使用了株Q-09的“Quimia,MX”制的“Nemaquim(注册商标)”)、多粘类芽孢杆菌(Paenibacillus polymyxa)(例如,使用了株AC-1的“GreenBiotech Company Ltd.”制的“Topseed(注册商标)”)、Paenibacillus poppiliae(例如,“St.Gabriel Laboratories”制的“Milky spore disease(注册商标)”)、拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)(例如,“Pasteuria Bioscience”制的“oyacystLF/ST(注册商标)”、使用了株Pn1的“Syngenta”制的“Clariva pn”)、穿刺巴氏杆菌(Pasteuriapenetrans)(例如,“Pasteuria Bioscience”制的“Pasteuria(注册商标)”)、Pasteuriausagae(例如,“Pasteuria Bioscience”制的“Econem(注册商标)”)、成团泛菌(Pantoeaagglomerans)(例如,使用了株E325的“Nufarm US”制的“Bloomtime Biological FDBiopesticide”)、胡萝卜软腐病果胶杆菌(Pectobacterium carotovorum)(例如,“日产化学(株式会社)”制的“BioKeeper(注册商标)”、使用了CGE234M403株的“KUMIAI CHEMICALINDUSTRY”制的“Ecomate(注册商标)”)、Phoma macrostroma(例如,使用了株94-44B的“Scotts,US”制的“Phoma H(注册商标)”)、拜赖青霉(Penicillium bilaii)(例如,“Novozymes”制的“Jump Start(注册商标)”)、大拟射脉菌(Phlebiopsis gigantea)(例如,使用了株FOC PG B22/SP1190/3.2的“Verdera,Finland”制的“ROTSOP(注册商标)”)、Pochonia chlamydosporia var.catenulata(例如,“The National Center of Animaland Plant Health(CENSA);CU”制的“KlamiC(注册商标)”)、金色假单胞菌(Pseudomonasaureofaciens)(例如,使用了株TX-1的“Eco Soils Systems,CA”制的“Spot-LessBiofungicide(注册商标)”)、绿针假单胞菌(Pseudomonas chlororaphis)(例如,使用了株63-28的“EcoSoil Systems”制的“ATEze(注册商标)”、使用了株MA 342的“Bioagri,S”制的“Cedomon(注册商标)”)、荧光假单胞菌(Pseudomonas fluorescens)(例如,使用了株1629RS的“Frost Technology Corp”制的“Frostban D(注册商标)”、使用了株A506的“Blightban”制的“Blightban(注册商标)”、使用了株FPT-9601的“多木化学(株式会社)”制的“Konae Fukudo(注册商标)”、作为株FPT-9601和株FPH-9601的混合物的“多木化学(株式会社)”制的“Cell Nae Genki(注册商标)”、使用了株G7090的“Arysta Life Science(株式会社)”制的“Vegikeeper(注册商标)”)、Pseudomonas proradix(例如,“Sourcon Padena”制的[Proradix(注册商标)])、食树脂假单胞菌(Pseudomonas resinovorans)(例如,“Agricultural Research Council,SA”制的“Solanacure(注册商标)”)、丁香假单胞菌(Pseudomonas syringae)(例如,使用了株MA-4的“EcoScience,US”制的“Biosave(注册商标)”、使用了株742RS的“Frostban C”制的“Frost Technology Corp(注册商标)”、使用了株ESC10的“Jet Harvest Systems”制的“Bio-save 10LP Biological Fungicide”、使用了株ESC11的“Jet Harvest Systems”制的“Bio-Save 11LP Biological Fungicide”)、假单胞菌属(Pseudomonas spp.)(例如,使用了HAI-0804株的“NIPPON SODA(株式会社)”制的“Masterpiece Wettable Powder(注册商标)”、使用了株CAB-02的“日产化学工业(株式会社)”制的“Momigenki Wettable Powder”)、Pseudozyma aphidis(例如,“YissumResearchDevelopment Company of the Hebrew University of Jerusalem”制)、Pseudozymaflocculosa(例如,使用了株PF-A22 UL的“Plant Products Co.Ltd,CA”制的“Sporodex L(注册商标)”)、寡雄腐霉(Pythium oligandrum)(例如,使用了株DV74或M1的“Bioprepraty,CZ”制的“Polyversum(注册商标)”)、Reynoutria sachlinensis(例如,“Marrone BioInnovations,US”制的“REGALIA(注册商标)”)、阿米尔氏须腹菌(Rhizopogonamylopogon)(例如,“Helena Chemical Company”制的“Myco-Sol(注册商标)”)、Rhizopogon fulvigleba(例如,“Helena Chemical Company”制的“Myco-Sol(注册商标)”)、酿酒酵母(Saccharomyces cerevisiae)(例如,“Lesaffre et Compagnie,FR”制)、小核盘菌(Sclerotinia minor)(例如,“Agrium Advanced Technologies”制的“Sarritor(注册商标)”)、嗜虫沙雷氏菌(Serratia entomophila)(例如,“Wrightson Seeds”制的“Invade(注册商标)”)、虫生簇孢(Sporothrix insectorum)(例如,“Biocerto;BR”制的“Sporothrix Es(注册商标)”)、小卷蛾斯氏线虫(Steinernema carpocapsae)(例如,“SDSBiotech(株式会社)”制的“Biosafe(注册商标)”)、Steinernema kushidai(例如,“(株式会社)KUBOTA”制的“Shibaichi Nema”)、格氏线虫(Steinernema glaseri)(例如,“ArystaLife Science(株式会社)”制的“Biotopia(注册商标)”)、酸性疮痂链霉菌(Streptomycesacidiscabies)(例如,使用了株RL-110T的“Marrone Bioinnovations,CA”制的“MBI-005EP(注册商标)”)、纯白链霉菌(Streptomyces candidus)(例如,使用了株Y21007-2的“Biontech,TW”制的“BioBac(注册商标)”)、鲜黄链霉菌(Streptomyces galbus)(例如,株K61“Verdera”制的“Mycostop(注册商标)”)、利迪链霉菌(Streptomyces lydicus)(例如,使用了株WYEC108的“Natural Industries,US”制的“ACTINOVATE(注册商标)”)、萨腊赛链霉菌(Streptomyces saraceticus)(例如,“A&AGroup(Agro ChemicalCorp.)”制的“Clanda(注册商标)”)、黄色蠕形霉(Talaromyces flavus)(例如,使用了株B-422的“CentralGlass(株式会社)”制的“Momikeeper(注册商标)”、使用了株SAY-Y-94-01的“发光兴产(株式会社)”制的“Tough Block(注册商标)”、使用了株V117b的“Prophyta,DE”制的“PROTUS(注册商标)WG”)、棘孢木霉(Trichoderma asperellum)(例如,使用了株ICC 012的“Isagro”制、使用了株T34的“Bioncontrol Technologies,ES”制的“T34 Biocontrol(注册商标)”、使用了株SKT-1的“KUMIAI CHEMICAL INDUSTRY工业(株式会社)”制的“ECO-HOPE(注册商标)”)、深绿木霉(Trichoderma atroviride)(例如,“Agrauxine,FR”制的“Esquive(注册商标)WP”、使用了株LC52的“Agrimm Technologies Ltd,NZ”制的“Tenet(注册商标)”或“SENTINEL(注册商标)”、使用了株SKT-1的“KUMIAI CHEMICAL INDUSTRY工业株式会社”制的“ECO HOPE DJ(注册商标)”)、盖姆斯木霉(Trichoderma gamsii)(例如,“BayerCropScienceLP,US”制的“BIO-TAMTM(注册商标)”)、哈茨木霉(Trichoderma harzianum)(例如,使用了株DB 103的“Dagutat Biolab”制的“T-Gro 7456(注册商标)”、使用了株ITEM908的“Koppert”制的“Trianum-P(注册商标)”、使用了株KD的“Biological ControlProducts,SA”制的“Trichoplus(注册商标)”、使用了株TH-35的“Mycontrol Ltd.”制的“ROOT PRO(注册商标)”)、哈茨木霉(Trichoderma harzianum rifai)(例如,使用了株T-22的“Firma BioWorks Inc.US”制的“PLANTSHIELD T-22G(注册商标)”、使用了株T-39的“Makhteshim Ltd,US”制的“TRICHODEX(注册商标)”)、木素木霉(Trichoderma lignorum)(例如,使用了株TL-0601的“Futureco Bioscience,ES”制的“Mycotric(注册商标)”)、多孢木霉(Trichoderma polysporum)(例如,“BINAB Bio-Innovation AB,Sweden”制的“BinabTFWP(注册商标)”)、钩木霉(Trichoderma stromaticum)(例如,“Ceplac;Brazil”制的“TRICOVAB(注册商标)”)、绿木霉菌(Trichoderma virens)(例如,使用了株GL-21的“Certis LLC,US”制的“SOILGARD(注册商标)”)、绿色木霉(Trichoderma viride)(例如,使用了株ICC080的“Isagro Ricerca,ITALIA”制的“REMEDIER(注册商标)WP”、使用了株TV1的“Koppert”制的“Trianum-P(注册商标)”)、微变冢村氏菌(Tsukamurella paurometabola)(例如,使用了株C-924的“HeberNem(注册商标)”)、奥德曼细基格孢(Ulocladiumoudemansii)(例如,使用了株HRU3的“Botry-Zen Ltd,NZ”制的“Botry-Zen(注册商标)”、使用了株U3的“BioWorks Inc.”制的“BotryStop”)、争论多噬菌(Variovorax paradoxus)(例如,使用了株CGF4526的“Central Glass”制的“Field keeper Wettable Powder(注册商标)”)、VA(泡囊丛枝菌根(Vesicular-Arbuscular Mycorrhiza)菌根菌(例如,“IDEMITSUAGRI”制的“Dr Kincon(注册商标)”)、黑白轮枝孢菌(Verticillium alboatrum)(例如,使用了株WCS850的“Tree Care Innovations”制的“Dutch Trig(注册商标)”)、蜡蚧轮枝菌(Verticillium lecanii)(例如,使用了株IMI 179172的“Arysta Life Science(株式会社)”制的“Vertalec(注册商标)”、使用了株IMI 263817的“Arysta Life Science(株式会社)”制的“Mycotal(注册商标)”)、野油菜黄单胞菌(Xanthomonas campestris)(例如,“多木化学”制的“Camperico L(注册商标)”)、Xanthomonas campestris pv poae、嗜菌异小杆线虫(Heterorhabditis bacteriophora)、夜蛾斯氏线虫(Steinernema feltiae)、Steinernema kraussei、Steinernema riobrave、蝼蛄斯氏线虫(Steinernemascapterisci)和选自具有各个株的识别特性的全部的这些株的变异株的杀虫·灭菌性株、以及针对植物病原性菌显示活性的、由各个株产生的代谢产物。
此外,还可与下述因素组合使用:丽蚜小蜂、科列马阿布拉小蜂(Aphidiuscolemani)、食蚜瘿蚊(Aphidoletes aphidimyza)、豌豆潜叶蝇姬小蜂(Diglyphus isaea)、西伯利亚离颚茧蜂(Dacnusa sibirica)、智利小植绥螨(Phytoseiulus persimilis)、黄瓜钝绥螨(Amblyseius cucumeris)、东亚小花蝽(Orius sauteri)等天敌生物、卵孢白僵菌(Beauveria brongniartii)等微生物农药、(Z)-10-十四碳烯乙酸酯、(E,Z)-4,10-十四碳二烯乙酸酯、(Z)-8-十二碳烯乙酸酯、(Z)-11-十四碳烯乙酸酯、(Z)-13-二十碳-10-酮、14-甲基-1-十八碳烯等信息素。
以下根据本发明的代表性化合物和制造中间体的制造例来更详细地进行说明,但是本发明不限于这些例子。
实施例
参考例1. 4-七氟异丙基咪唑的制造方法
[化学式23]
将咪唑(1.0g,15mmol)溶解在乙酸乙酯(25mL)中,在35℃下添加水(25mL)、碳酸钾(6.1g,44mmol)、七氟异丙基碘(3.1mL,22mmol)和连二亚硫酸钠(1.3g,7.4mmol)。在35℃下使反应溶液进行3.5小时反应后,用乙酸乙酯进行提取,用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(1.3g,37%)。
参考例2. 2-(4-七氟异丙基咪唑-1-基)苯并咪唑的制造方法
[化学式24]
将4-七氟异丙基咪唑(1.27g,5.36mmol)、2-羟基苯并咪唑(0.863g,6.43mmol)和三氯氧磷(5.00mL)进行5.5小时回流。将反应溶液放冷至室温后,向2.0M的氢氧化钠水溶液(100mL)中滴加反应溶液。然后,使用氯化铵进行中和,用甲苯提取。用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(1.28g,68%)。
实施例1. 1-乙烷磺酰基-2-(4-七氟异丙基咪唑-1-基)苯并咪唑的制造方法(化合物编号1-22)
[化学式25]
将2-(4-七氟异丙基咪唑-1-基)苯并咪唑(985mg,2.80mmol)溶解于THF(5.0mL),在室温下分多次加入氢化钠(134mg,3.36mmol)。5分钟后,在室温下添加乙烷磺酰氯(449μL,4.76mmol),反应4小时。然后,用水终止反应,用乙酸乙酯进行提取。用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(246mg,20%)。
参考例3. 1-甲氧基甲基-2-(4-羟基甲基咪唑-1-基)苯并咪唑的制造方法
[化学式26]
代替参考例12的SEMCl(2-(三甲基甲硅烷基)乙氧基甲基氯)而使用由MOMCl制造的1-甲氧基甲基-2-氯苯并咪唑并使用4-甲酰基咪唑,根据参考例7的制造方法制造1-甲氧基甲基-2-(4-甲酰基咪唑-1-基)苯并咪唑(1.16g,4.48mmol),将其溶解在甲醇(10mL)中,在室温下一点一点添加NaBH4(339mg,8.96mmol),反应1小时后,用水终止反应。用乙酸乙酯进行提取,得到目标产物(1.04g,90%)。
参考例4. 1-甲氧基甲基-2-(4-苯氧基甲基咪唑-1-基)苯并咪唑的制造方法
[化学式27]
将1-甲氧基甲基-2-(4-羟基甲基咪唑-1-基)苯并咪唑(302mg,1.17mmol)溶解在甲苯(5mL)中,在0℃下添加三苯基膦(399mg,1.52mmol)、DEAD(偶氮二羧酸二乙基)(691μL,1.52mmol)、苯酚(268μL,3.04mmol)。将反应溶液升温至室温,反应4小时。用水终止反应后,用乙酸乙酯进行提取,得到目标产物。
参考例5. 2-(4-苯氧基甲基咪唑-1-基)苯并咪唑的制造方法
[化学式28]
通过与参考例11相同的方法,制造2-(4-苯氧基甲基咪唑-1-基)苯并咪唑。
实施例2. 1-乙烷磺酰基-2-(4-苯氧基甲基咪唑-1-基)苯并咪唑的制造方法(化合物编号1-15)
[化学式29]
通过与实施例1相同的方法制造1-乙烷磺酰基-2-(4-苯氧基甲基咪唑-1-基)苯并咪唑。
参考例6. 3-三氟甲基-1H-吡唑-4-羧酸叔丁酯的制造方法
[化学式30]
将WO2009134750号小册子所述的3-三氟甲基-1H-吡唑-4-羧酸(1.0g,5.6mmol)溶解在甲苯(28mL)中,在室温下添加N,N-二甲基甲酰胺二-叔丁基缩醛(6.7mL,28mmol)。将反应溶液进行4小时加热回流,然后,放冷至室温。将反应溶液浓缩,通过柱层析对得到的粗生成物进行纯化,得到目标产物(0.89g,3.8mmol,68%)。
参考例7. 1-(2-(三甲基甲硅烷基)乙氧基甲基)-2-(4-叔丁氧基羰基-3-三氟甲基-1H-吡唑-1-基)苯并咪唑的制造方法
[化学式31]
将3-三氟甲基-1H-吡唑-4-羧酸叔丁酯(1.47g,3.05mmol)溶解至NMP(6.0mL),在室温下添加通过参考例12的方法制造的1-(2-(三甲基甲硅烷基)乙氧基甲基)-2-氯苯并咪唑(1.18g,4.16mmol)、碳酸钾(1.04g,7.56mmol)。将反应溶液在120℃下进行6小时反应,然后,放冷至室温。将乙酸乙酯、水添加至反应溶液中。用乙酸乙酯进行提取操作后,用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(1.48g,81%)。
参考例8. 2-(4-叔丁氧基羰基-3-三氟甲基-1H-吡唑-1-基)苯并咪唑的制造方法
[化学式32]
将1-(2-(三甲基甲硅烷基)乙氧基甲基)-2-(4-叔丁氧基羰基-3-三氟甲基-1H-吡唑-1-基)苯并咪唑(1.47g,3.05mmol)溶解在THF/NMP(1:1,10mL)中,在室温下添加TBAF(四丁基氟化铵)(1.0M的THF溶液,6.0mL,6.00mmol)。将反应溶液在90℃下反应3小时,然后,放冷至室温,将乙酸乙酯、水添加至反应溶液中。用乙酸乙酯进行提取操作后,用硫酸镁对有机层进行干燥,蒸馏除去溶剂。得到的粗生成物原样用于下一反应。
实施例3. 1-乙烷磺酰基-2-(4-叔丁氧基羰基-3-三氟甲基-1H-吡唑-1-基)苯并咪唑的制造方法(化合物编号2-27)
[化学式33]
将2-(4-叔丁氧基羰基-3-三氟甲基-1H-吡唑-1-基)苯并咪唑(1.20g,3.41mmol)溶解在THF(10.0mL)中,在室温下分多次添加氢化钠(177mg,4.43mmol)。5分钟后,在室温下添加乙烷磺酰氯(645μL,6.82mmol),进行2小时反应。然后,用水终止反应,用乙酸乙酯进行提取。用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(266mg,18%(2工序))。
参考例9. 4-溴-3-三氟甲基-1H-吡唑的制造方法
[化学式34]
将3-三氟甲基-1H-吡唑(1.4g,10mmol)和DBH(1,3-二溴-5、5-二甲基乙内酰脲)(1.7g,6.0mmol)添加至乙腈(20mL)中,在回流下反应3小时。冷却后,用饱和硫代硫酸钠水溶液进行淬火,用碳酸钾水溶液进行中和,用乙酸乙酯进行提取。用饱和食盐水清洗有机层,用硫酸钠进行干燥。将溶剂蒸馏除去,得到目标产物(2.1g)。不纯化而用于接下来的工序。
参考例10. 1-甲氧基甲基-2-(4-溴-3-三氟甲基-1H-吡唑-1-基)苯并咪唑的制造方法
[化学式35]
将4-溴-3-三氟甲基-1H-吡唑(0.54g,2.5mmol)、根据参考例12的方法将SEMCl(2-(三甲基甲硅烷基)乙氧基甲基氯)变更为MOMCl而制造得到的1-甲氧基甲基-2-氯苯并咪唑(0.49g,2.5mmol)、以及碳酸钾(1.0g,7.5mmol)添加至NMP(10mL)。在120℃下反应3小时。冷却至室温后,添加水,用乙酸乙酯进行提取。用饱和食盐水清洗有机层,用硫酸钠进行干燥。蒸馏除去溶剂后,通过柱层析进行纯化,得到目标产物(0.54g,54%(2工序))。
参考例11. 2-(4-溴-3-三氟甲基)-1H-吡唑-1-基)苯并咪唑的制造方法
[化学式36]
将1-甲氧基甲基-2-(4-溴-3-三氟甲基-1H-吡唑-1-基)苯并咪唑(0.50g,1.3mmol)添加至甲醇(20mL),添加浓盐酸(10mL)。然后,在回流下反应2小时。冷却至室温后,添加碳酸钾水溶液进行中和,用乙酸乙酯进行提取。用饱和食盐水溶剂清洗有机层,用硫酸钠进行干燥。蒸馏除去溶剂,得到目标产物(0.36g,82%)。
实施例4. 1-乙烷磺酰基-2-(4-溴-3-三氟甲基)-1H-吡唑-1-基)苯并咪唑的制造方法(化合物编号2-14)
[化学式37]
将2-(4-溴-3-三氟甲基-1H-吡唑-1-基)苯并咪唑(0.15g,0.44mmol)添加至THF(10mL),添加60%氢化钠(26mg,0.66mmol)。消泡后,滴加乙烷磺酰氯(0.11g,0.88mmol),反应30分钟。然后添加三乙胺(1.0mL),进一步反应1小时。添加饱和氯化铵水溶液进行淬火,用乙酸乙酯进行提取。以三乙胺/水、饱和食盐水的顺序清洗有机层,用硫酸钠进行干燥。蒸馏除去溶剂后,通过柱层析进行纯化,得到目标产物(98mg,53%)。
参考例12. 2-氯-1-(2-(三甲基甲硅烷基)乙氧基甲基)苯并咪唑的制造方法
[化学式38]
将2-氯苯并咪唑(10.0g,74.6mmol)溶解至DMA(60mL),在室温下分多次添加氢化钠(3.58g,89.5mmol)。反应5分钟后,在室温下添加SEMCl(2-(三甲基甲硅烷基)乙氧基甲基氯)(17.3mL,97.8mmol)。在室温下反应3小时后,用水终止反应。用乙酸乙酯进行提取,用硫酸镁对有机层进行干燥,蒸馏除去溶剂。将得到的粗生成物通过柱层析进行纯化,得到目标产物(16.7g,79%)。
下文中示出制剂的实施例,但不限于此。在制剂例中,所记载的份表示重量份。
制剂例1.
本发明化合物 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与烷基苯磺酸钙的混合物 10份
将以上均匀地混合溶解,制成乳剂。
制剂例2.
本发明化合物 3份
黏土粉末 82份
硅藻土粉末 15份
将以上均匀地混合粉碎,制成粉剂。
制剂例3.
本发明化合物 5份
膨润土与黏土的混合粉末 90份
木质素磺酸钙 5份
将以上均匀地混合,添加适量的水进行混炼、造粒、干燥,制成粒剂。
制剂例4.
本发明化合物 20份
高岭土与合成高分散硅酸 75份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物 5份
将以上均匀地混合粉碎,制成可湿性粉剂。
制剂例5.
本发明化合物 20份
聚氧乙烯月桂基醚 3份
磺基琥珀酸钠二辛酯 3.5份
二甲亚砜 37份
2-丙醇 36.5份
将以上均匀地混合溶解,制成水溶性浓缩剂调制物。
制剂例6.
本发明化合物 2份
二甲亚砜 10份
2-丙醇 35份
丙酮 53份
将以上均匀地混合溶解,制成喷雾用液剂。
制剂例7.
本发明化合物 5份
己二醇 50份
异丙醇 45份
将以上均匀地混合溶解,制成透皮给药用液剂。
制剂例8.
本发明化合物 5份
丙二醇单甲醚 50份
二丙二醇 45份
将以上均匀地混合溶解,制成透皮给药用液剂。
制剂例9.
本发明化合物 2份
轻质液体石蜡 98份
将以上均匀地混合溶解,制成透皮给药(泼浇)用液剂。
制剂例10.
本发明化合物 2份
轻质液体石蜡 58份
橄榄油 30份
ODO-H 9份
信越聚硅氧烷 1份
将以上均匀地混合溶解,制成透皮给药(泼浇)用液剂。
接下来,将示出本发明的试验例,但不限于此。
试验例1.
对桃蚜(Myzus persicae)的防治值试验
将白菜种植在直径8cm、高度8cm的塑料盆(Plastic pot)中,使桃蚜繁殖,调查各个盆的寄生虫数。将本发明的通式(1)表示的苯并咪唑化合物或其盐类分散在水中并稀释为500ppm的药液,将该药液散布于种植在盆中的白菜的茎叶上并风干后,将盆保管于温室下,在药剂散布后第6天,调查寄生于各白菜的桃蚜的寄生虫数,通过下述数学式计算防治值,根据下述判定基准进行判定。
[数学式1]
防治值=100-{(T×Ca)/(Ta×C)}×100
Ta:处理区的散布前寄生虫数
T:处理区的散布后寄生虫数
Ca:无处理区的散布前寄生虫数
C:无处理区的散布后寄生虫数
判定基准
A···防治值100%
B···防治值99%~90%
C···防治值89%~80%
D···防治值79%~50%
其结果,本发明化合物的1-4、1-6、1-8、1-12、1-13、1-24、1-25、1-26、1-27、1-30、1-32、2-8、2-10、2-11、2-13、2-15、2-19、2-20、2-24、2-26、2-28、2-34、2-39、2-40、2-43、2-51、2-53、2-54和3-1的化合物表现出D以上的活性。
试验例2.对灰飞虱(Laodelphax striatella)的杀虫试验
将本发明的通式(1)表示的苯并咪唑化合物或其盐类分散于水中并稀释为500ppm的药液,用该药液将水稻幼苗(品种:日本晴)浸渍30秒,风干后放入玻璃试管中,分别接种10只灰飞虱3龄幼虫后,用棉塞塞住,在接种8天后根据活虫和死虫的数量来调查生存率,通过下述数学式计算校正死虫率,根据下述判定基准进行判定。
[数学式2]
判定基准
A···死虫率100%
B···死虫率99%~90%
C···死虫率89%~80%
D···死虫率79%~50%
其结果,本发明化合物的1-9、1-13、1-22、1-25、1-26、1-27、1-28、1-30、2-12、2-13、2-17、2-18、2-19、2-20、2-21、2-26、2-29、2-32、2-34、2-47、2-48、2-51、2-52、2-53和2-54的化合物表现出D以上的活性。
试验例3.对小菜蛾(Plutella xylostella)杀虫试验
将小菜蛾的成虫放养于白菜幼苗上并使其产卵,在放养2天后,将附有产下卵的白菜幼苗浸渍于药液中约30秒,在风干后于25℃的恒温室静置,所述药液通过将以本发明的通式(1)表示的苯并咪唑化合物或其盐类为有效成分的药剂稀释至500ppm而得到。在浸渍药液起6天后,调查孵化虫数,通过下述数学式计算校正死虫率,根据试验例2的判定基准进行判定。1区10只3连制。
[数学式3]
其结果,本发明化合物的1-11、1-30、2-3、2-8、2-11、2-18、2-23、2-38、2-39、2-43、2-47、2-48、2-49、2-51和2-52的化合物表现出D以上的活性。
试验例4.对二斑叶螨(Tetranychus urticae)的杀螨试验。
用菜豆叶制成直径2cm的叶盘,放置于湿润滤纸上,向其接种雌成虫后,将药液50ml均匀地散布在转盘上,散布后在25℃的恒温室静置,所述药液通过将以本发明的通式(1)表示的苯并咪唑化合物或其盐类为有效成分的药剂稀释至500ppm而得到。在药剂处理起2天后,调查死亡虫数,并通过下述式计算校正死虫率,根据试验例2的判定基准进行判定。1区10只2连制。
[数学式4]
其结果,本发明化合物的1-2、1-3、1-4、1-5、1-6、1-7、1-8、1-9、1-10、1-11、1-12、1-13、1-14、1-16、1-17、1-18、1-20、1-21、1-22、1-23、1-24、1-25、1-27、1-28、1-31、1-32、1-33、1-36、1-37、1-38、1-39、1-40、1-41、1-42、1-43、1-44、1-45、1-46、2-2、2-3、2-4、2-5、2-6、2-7、2-8、2-9、2-10、2-11、2-12、2-13、2-14、2-15、2-16、2-17、2-18、2-19、2-20、2-21、2-22、2-23、2-24、2-25、2-26、2-28、2-29、2-30、2-31、2-32、2-33、2-34、2-35、2-36、2-37、2-38、2-39、2-40、2-41、2-42、2-43、2-44、2-45、2-47、2-48、2-49、2-50、2-51、2-52、2-53、2-54、2-55、2-56、2-57、2-58、2-59、2-61、2-62、2-72、2-73、2-74、2-76、2-77、2-78、2-79、2-80、2-81、2-82、2-83、2-84、2-85、2-86、2-87、2-88、2-89、2-90、2-91、2-92、2-93、2-94、2-95、2-96、2-97、2-98、2-99、2-100、2-101、2-102、2-103、2-104、2-105、2-106、2-107、2-108、2-109、2-110、2-111、2-112、2-113、2-114、2-115、2-116、2-117、2-118、2-119、2-120、2-121、2-122、2-123、2-124、2-125、2-126、2-127、2-128、2-129、2-130、2-131、2-132、2-133、2-134、2-135、2-136、2-137、2-138、2-139、2-140、2-141、2-142、2-143、2-144、2-145、3-1、3-2、3-4、7-1和7-6的化合物表现出D以上的活性。
试验例5.对捻转血茅线虫(Haemonchus contortus)的幼虫运动的影响评价试验
将本发明的通式(1)表示的苯并咪唑化合物或其盐类的DMSO稀释溶液添加至包含给定的调制液的96孔板的各孔中,并使得最终浓度为50ppm。放养20只捻转血茅线虫的L-1阶段幼虫,在静置4天后,调查其运动能力。以仅DMSO溶液具有的抑制能力为基准来校正并计算各处理区的运动抑制率,根据下述判定基准进行判定。
判定基准
A···校正运动抑制率100%
B···校正运动抑制率99%~90%
C···校正运动抑制率89%~80%
D···校正运动抑制率79%~50%
其结果,本发明化合物的1-13、1-17、1-28、2-2、2-4、2-8、2-14和2-34表现出A的活性。
试验例6.对犬恶丝虫(Dirofilaria immitis)的幼虫运动的影响评价试验
将用给定的调制液进行了稀释的500只犬恶丝虫的L-1阶段幼虫接种至96孔板的各孔中,添加本发明的通式(1)表示的苯并咪唑化合物或其盐类的DMSO稀释溶液并使得最终浓度为50ppm。然后,静置3天,调查其运动能力。以仅DMSO溶液具有的抑制能力为基准来校正并计算各处理区的运动抑制率,根据下述判定基准进行判定。
判定基准
A···校正运动抑制率100%
B···校正运动抑制率99%~90%
C···校正运动抑制率89%~80%
D···校正运动抑制率79%~50%
其结果,本发明化合物的1-13、1-17、1-28、2-2、2-4、2-8、2-14和2-34表现出A的活性。
工业实用性
本发明的化合物对广泛的农业园艺中的害虫、螨类具有优异的防治效果,并且是有用的。
Claims (7)
1.一种苯并咪唑化合物或其盐类,其由下述化学式1表示,
[化学式1]
式1中,R表示:
(a1)(C1-C6)烷基;
(a2)(C3-C6)环烷基;
(a3)(C3-C6)环烷基(C1-C6)烷基;
(a4)卤代(C1-C6)烷基;
(a5)(C2-C6)烯基;或
(a6)(C2-C6)炔基,
Y1、Y2、Y3和Y4可以相同或不同,并且表示:
(b1)氢原子;
(b2)卤素原子;
(b3)(C1-C6)烷基;或
(b4)卤代(C1-C6)烷基,
Q选自以下的含氮5元环杂环基,
[化学式2]
式2中,X1和X4可以相同或不同,并且表示:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X2表示:
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)(C1-C12)烷基;
(d5)(C3-C6)环烷基;
(d6)(C2-C12)烯基;
(d7)(C2-C12)炔基;
(d8)(C1-C6)烷氧基;
(d9)卤代(C1-C6)烷基;
(d10)卤代(C1-C6)烷氧基;
(d11)(C1-C6)烷基硫基;
(d12)(C1-C6)烷基亚磺酰基;
(d13)(C1-C6)烷基磺酰基;
(d14)卤代(C1-C6)烷基硫基;
(d15)卤代(C1-C6)烷基亚磺酰基;
(d16)卤代(C1-C6)烷基磺酰基;
(d17)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d19)(C1-C6)烷基羰基;
(d20)(C1-C6)烷氧基羰基;
(d21)(C2-C6)炔氧基羰基;
(d22)(C1-C6)烷基硫基羰基;
(d23)(C1-C6)烷氧基羰基(C1-C6)烷基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d25)芳氧基(C1-C6)烷基;
(d26)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C1-C6)烷基;
(d27)芳氧基羰基;
(d28)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(d29)芳基羰基;
(d30)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基羰基;
(d31)芳基(C1-C6)烷基;
(d32)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(d33)芳基(C1-C6)烷氧基羰基;
(d34)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d37)R1R2N基,此处R1和R2可以相同或不同,并且表示:(aa)氢原子、(ab)(C1-C6)烷基、(ac)(C1-C6)烷氧基、(ad)(C1-C6)烷氧基羰基、(ae)(C1-C6)烷基磺酰基、(af)卤代(C1-C6)烷基磺酰基、(ag)芳基、(ah)(C3-C6)环烷基、(ai)卤代(C1-C6)烷基、(aj)芳基(C1-C6)烷基;
(d38)R1R2N羰基,此处R1和R2与上述相同;
(d39)R1R2N磺酰基,此处R1和R2与上述相同;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d44)(C3-C12)环烷基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d47)(C3-C6)环烷基(C1-C6)烷基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d51)(C1-C6)烷基羰氧基(C1-C6)烷基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基;
(d55)1-(C1-C6)烷氧基亚氨基(C1-C6)烷基;
(d56)(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d57)卤代(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d58)芳基(C1-C6)烷基硫基;或
(d59)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基硫基,
X3表示:
(e1)氢原子;
(e2)卤素原子;
(e3)(C1-C6)烷基;
(e4)卤代(C1-C6)烷基;
(e5)(C1-C6)烷氧基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e8)(C1-C6)烷基硫基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e10)(C1-C6)烷氧基羰基;
(e11)(C2-C6)炔氧基羰基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e14)芳基磺酰基;
(e15)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基磺酰基;
(e16)芳氧基羰基;
(e17)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(e18)芳基(C1-C6)烷氧基羰基;
(e19)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基;
(e20)芳基(C1-C6)烷氧基;
(e21)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e28)(C1-C6)烷氧基(C1-C6)烷基;
(e29)(C2-C6)炔氧基;
(e30)氰基;
(e31)(C2-C6)炔基;
(e32)(C1-C6)烷氧基羰基(C1-C6)烷基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基;
(e35)R1R2N羰基,此处R1和R2与上述相同;
(e36)R1R2N羰基(C1-C6)烷氧基,此处R1和R2与上述相同;或
(e37)R1R2N羰基卤代(C1-C6)烷氧基,此处R1和R2与上述相同,
X2可以与X3键合,与它们键合的碳原子一同形成5~8元的脂肪族环,该脂肪族环可具有选自(C1-C6)烷基和羰基中的1~5个取代基,●符号的部分与苯并咪唑键合。
2.根据权利要求1所述的苯并咪唑化合物或其盐类,其中,
R表示:
(a1)(C1-C6)烷基;或
(a4)卤代(C1-C6)烷基,Y1、Y2、Y3和Y4可以相同或不同,并且表示:(b1)氢原子;
(b2)卤素原子;
(b3)(C1-C6)烷基;或
(b4)卤代(C1-C6)烷基,X1和X4可以相同或不同,并且表示:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X2表示:
(d1)氢原子;
(d2)卤素原子;
(d3)氰基;
(d4)(C1-C12)烷基;
(d5)(C3-C6)环烷基;
(d6)(C2-C12)烯基;
(d7)(C2-C12)炔基;
(d9)卤代(C1-C6)烷基;
(d11)(C1-C6)烷基硫基;
(d12)(C1-C6)烷基亚磺酰基;
(d13)(C1-C6)烷基磺酰基;
(d14)卤代(C1-C6)烷基硫基;
(d17)卤代(C1-C6)烷氧基(C1-C6)烷基;
(d18)(C3-C6)环烷基(C2-C6)炔基;
(d19)(C1-C6)烷基羰基;
(d20)(C1-C6)烷氧基羰基;
(d21)(C2-C6)炔氧基羰基;
(d22)(C1-C6)烷基硫基羰基;
(d23)(C1-C6)烷氧基羰基(C1-C6)烷基;
(d24)(C1-C6)烷氧基羰基(C2-C6)烯基;
(d25)芳氧基(C1-C6)烷基;
(d26)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C1-C6)烷基;
(d27)芳氧基羰基;
(d28)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基羰基;
(d29)芳基羰基;
(d30)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基羰基;
(d31)芳基(C1-C6)烷基;
(d32)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(d35)芳基(C2-C6)炔基;
(d36)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(d38)R1R2N羰基,此处R1和R2与上述相同;
(d39)R1R2N磺酰基,此处R1和R2与上述相同;
(d40)卤代(C1-C6)烷氧基羰基;
(d41)卤代(C1-C6)烷氧基羰基(C2-C6)烯基;
(d42)芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d43)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d44)(C3-C12)环烷基(C1-C6)烷氧基羰基(C2-C6)烯基;
(d45)杂芳基(C2-C6)炔基;
(d46)具有1~4个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的杂芳基(C2-C6)炔基;
(d47)(C3-C6)环烷基(C1-C6)烷基;
(d48)(C1-C6)烷氧基(C2-C6)炔基;
(d49)(C1-C6)烷氧基(C1-C6)烷基;
(d50)(C1-C6)烷基羰氧基(C2-C6)炔基;
(d51)(C1-C6)烷基羰氧基(C1-C6)烷基;
(d52)卤代(C1-C6)烷氧基(C2-C6)炔基;
(d53)芳氧基(C2-C6)炔基;
(d54)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳氧基(C2-C6)炔基;
(d56)(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d57)卤代(C1-C6)烷基氨基羰基(C2-C6)烯基;
(d58)芳基(C1-C6)烷基硫基;或
(d59)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基硫基,
X3表示:
(e1)氢原子;
(e2)卤素原子;
(e3)(C1-C6)烷基;
(e4)卤代(C1-C6)烷基;
(e5)(C1-C6)烷氧基;
(e6)卤代(C1-C6)烷氧基;
(e7)(C1-C6)烷氧基羰基(C2-C6)烯基;
(e8)(C1-C6)烷基硫基;
(e9)(C1-C6)烷氧基羰基(C1-C6)烷氧基;
(e10)(C1-C6)烷氧基羰基;
(e12)芳基(C1-C6)烷基;
(e13)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷基;
(e14)芳基磺酰基;
(e15)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基磺酰基;
(e20)芳基(C1-C6)烷氧基;
(e21)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C1-C6)烷氧基;
(e22)(C3-C6)环烷基;
(e23)(C3-C6)环烷基(C2-C6)烯基;
(e24)(C3-C6)环烷基(C1-C6)烷基;
(e25)(C2-C6)烯基;
(e26)芳基(C2-C6)炔基;
(e27)具有1~5个可以相同或不同的选自(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)烷基硫基、(g)卤代(C1-C6)烷基硫基、(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)烷基磺酰基中的取代基的芳基(C2-C6)炔基;
(e28)(C1-C6)烷氧基(C1-C6)烷基;
(e29)(C2-C6)炔氧基;
(e30)氰基;
(e31)(C2-C6)炔基;
(e32)(C1-C6)烷氧基羰基(C1-C6)烷基;
(e33)(C1-C6)烷氧基(C2-C6)炔基;
(e34)卤代(C1-C6)烷氧基(C2-C6)炔基;
(e35)R1R2N羰基,此处R1和R2与上述相同;
(e36)R1R2N羰基(C1-C6)烷氧基,此处R1和R2与上述相同;或
(e37)R1R2N羰基卤代(C1-C6)烷氧基,此处R1和R2与上述相同,
X2可以与X3键合,与它们键合的碳原子一同形成5~8元的脂肪族环,该脂肪族环可具有选自(C1-C6)烷基和羰基中的1~5个取代基。
3.根据权利要求1或2所述的苯并咪唑化合物或其盐类,其中,
Q为Q-2、Q-3或Q-4。
4.一种农艺和园艺用杀虫杀螨剂,其含有:
权利要求1~3中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
5.一种农艺和园艺用杀虫杀螨剂的使用方法,其中,
用有效量的权利要求1~3中任一项所述的苯并咪唑化合物或其盐类对植物或土壤进行处理。
6.一种用于动物的外部寄生虫防治剂,其含有:
权利要求1~3中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
7.一种用于动物的内部寄生虫防治剂,其含有:
权利要求1~3中任一项所述的苯并咪唑化合物或其盐类作为有效成分。
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WO2022255462A1 (ja) * | 2021-06-02 | 2022-12-08 | 日本農薬株式会社 | ベンゾイミダゾール化合物又はその塩類及び該化合物を含有する犬糸状虫症防除剤並びにその使用方法 |
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JP7483748B2 (ja) | 2024-05-15 |
KR20220108788A (ko) | 2022-08-03 |
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