CN116768796A - 一类新型吡唑-3-甲酰胺衍生物及其制备方法和用途 - Google Patents
一类新型吡唑-3-甲酰胺衍生物及其制备方法和用途 Download PDFInfo
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- CN116768796A CN116768796A CN202210232563.8A CN202210232563A CN116768796A CN 116768796 A CN116768796 A CN 116768796A CN 202210232563 A CN202210232563 A CN 202210232563A CN 116768796 A CN116768796 A CN 116768796A
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G13/00—Protecting plants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明提供了一类吡唑酰胺类衍生物及其制备方法和用途,本发明涉及5‑氯‑4‑二氟甲基‑吡唑‑3‑甲酰胺衍生物,它们具有如Ⅷ所示的化学结构通式。Ⅷ:
Description
技术领域
本发明的技术方案涉及吡唑酰胺类化合物,具体涉及5-氯-4-二氟甲基-吡唑-3-甲酰胺衍生物。
背景技术
杂环骨架应用作为农药分子合理设计的常规策略,在农药先导结构的优化中起重要作用。据统计,在农药结构中,有70%以上的分子至少含有1个杂环。吡唑作为常见的五元含氮杂环,其衍生物具有结构多样性,因而展示了多种生物活性,如杀虫、杀菌、除草、植物免疫诱导活性等(卢世超.农药,2020,59,397-406);相应的吡唑化合物已发展为杀菌剂品种。例如,琥珀酸脱氢酶抑制剂类杀菌剂品种中,具有典型的含二氟甲基吡唑结构(杨吉春.现代农药,2016,14(5):1-9),代表的品种有呋吡菌胺(furametpyr)、吡噻菌胺(penthiopyrad)、联苯吡菌胺(bixafen)、吡唑萘菌胺(isopyrazam)、氟唑环菌胺(sedaxane)、苯并烯氟菌唑(benzovindiflupyr)以及氟唑菌酰胺(fluxapyroxad)等。
在农用化学品中,酰胺结构是最为常见的官能团,展示多种药效功能,其衍生物具有抗菌、杀虫、除草、抗病毒等广泛的生物活性,其合成和生物活性研究一直是农药化学研究的热点(郑玉国.精细化工中间体,2015,45,1-10)。近年来国内外先后开发了多个具有酰胺结构的高选择性、高活性的除草剂、杀虫剂、抗菌剂以及抗病毒农药。例如,杀菌剂包括萎锈灵(Carboxin)、甲霜灵(Metalaxyl)、氟吡菌胺(Furametpyr)、吡噻菌胺(Penthiopyrad)、啶酰菌胺(Boscalid)等。因此,设计合成新型的酰胺类衍生物,探索其生物活性,有望发现更多高效的农药新品种。
吡唑酰胺类化合物主要含有吡唑环和酰胺键两个活性亚结构,具有潜在的生物活性,自20世纪40年代以来已有多种吡唑酰胺类化合物被开发为农药新品种。由于该类化合物结构易于衍生和修饰,已成为新农药研发的热门结构(翟志文.浙江工业大学,2017),具有非常广阔的开发前景。因此本发明设计和合成了一类新型吡唑-3-甲酰胺衍生物,同时进行了系统的生物活性筛选和评价,以期为新农药创制研究提供更多的高活性侯选化合物。
发明内容
本发明所要解决的技术问题是:提供一类新的吡唑酰胺衍生物的合成方法及其调控农业、园艺、卫生和林业植物害虫、植物病原物的生物活性及其测定方法,同时提供这些化合物在农业领域、园艺领域、林业领域以及卫生领域中的应用。
本发明解决该技术问题所采用的技术方案是:具有农业领域、园艺领域、林业领域杀虫、杀螨活性、杀菌活性、抗植物病毒活性、诱导植物产生抗病活性的吡唑酰胺类化合物的化学结构通式见式Ⅷ:
Ⅷ:
其中,R选自:氢,2-氟苯基,2-氯苯基,3-异丙氧基苯基,4-(三氟甲氧基)苯基,3-硝基苯酚-4-基,(1,1-联苯)-2-基,4-乙烯基-(1,1-联苯)-2-基,4-甲氧基-(1,1-联苯)-2-基,4-氟-(1,1-联苯)-2-基,3,4-二氟-(1,1-联苯)-2-基,4-甲基-3-氯-(1,1-联苯)-2-基,4-甲基-3,5-二氟-(1,1-联苯)-2-基,2-苯基吡啶-3-基,2-苯基吡啶-4-基,2-(4-甲氧基苯基)吡啶-5-基,2-苯氧基苯基,2-(邻甲苯氧基)苯基,5-氯-2-苯氧基苯基,5-氯-2-(4-氯苯氧基)苯基,2-(4-氯苯氧基)苯基,4-(4-甲氧基苯氧基)苯基,1-甲基-4-苯氧基苯基,3-苄氧基苯基,4-((5-(三氟甲基)吡啶-2-基)氧基)苯基,4-氟-2-(苯基氨基)苯基,4-氟-2-((4-(叔丁基)苯基)氨基)苯基,4-氟-2-((3-氟苯基)氨基)苯基,4-氟-2-((3-氟-2-甲氧基苯基)氨基)苯基,4-氟-2-((3-氟-4-甲基苯基)氨基)苯基,4-氟-2-((3,4-二氟苯基)氨基)苯基。
本发明的5-氯-4-二氟甲基-吡唑-3-甲酰胺衍生物Ⅷ的合成方法如下:
其中,R选自:2-氟苯基,2-氯苯基,3-异丙氧基苯基,4-(三氟甲氧基)苯基,3-硝基苯酚-4-基,(1,1-联苯)-2-基,4-乙烯基-(1,1-联苯)-2-基,4-甲氧基-(1,1-联苯)-2-基,4-氟-(1,1-联苯)-2-基,3,4-二氟-(1,1-联苯)-2-基,4-甲基-3-氯-(1,1-联苯)-2-基,4-甲基-3,5-二氟-(1,1-联苯)-2-基,2-苯基吡啶-3-基,2-苯基吡啶-4-基,2-(4-甲氧基苯基)吡啶-5-基,2-苯氧基苯基,2-(邻甲苯氧基)苯基,5-氯-2-苯氧基苯基,5-氯-2-(4-氯苯氧基)苯基,2-(4-氯苯氧基)苯基,4-(4-甲氧基苯氧基)苯基,1-甲基-4-苯氧基苯基,3-苄氧基苯基,4-((5-(三氟甲基)吡啶-2-基)氧基)苯基,4-氟-2-(苯基氨基)苯基,4-氟-2-((4-(叔丁基)苯基)氨基)苯基,4-氟-2-((3-氟苯基)氨基)苯基,4-氟-2-((3-氟-2-甲氧基苯基)氨基)苯基,4-氟-2-((3-氟-4-甲基苯基)氨基)苯基,4-氟-2-((3,4-二氟苯基)氨基)苯基。
本发明的5-氯-4-二氟甲基-吡唑-3-甲酰胺衍生物的合成以及生物活性测定的具体方法分为以下步骤:
A.化合物Ⅱ的制备:
在100毫升单口圆底烧瓶中加入33.38毫摩尔化合物I和41.73毫摩尔甲基肼硫酸盐,加入12毫升甲苯和12毫升冰乙酸溶解,再加入83.45毫摩尔乙酸钠,100℃搅拌1.5小时,反应完全后减压除去溶剂,残余物经100~200目硅胶柱层析纯化得化合物Ⅱ,洗脱剂为二氯甲烷:乙酸乙酯,体积比为5:1,收率85-95%;化合物Ⅱ制备的量和反应容器的体积按相应比例扩大或缩小。
B.化合物III的制备:
在100毫升单口圆底烧瓶中加入8.29毫摩尔化合物Ⅱ和33.16毫摩尔N,N-二甲基甲酰胺溶液,再向反应中加入66.32毫摩尔三氯氧磷,然后90℃加热回流3小时,反应结束后将反应液倒入冰水中,加入碳酸氢钠直至混合物不产生气泡。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤,减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率80-90%;化合物Ⅲ制备的量和反应容器的体积按相应比例扩大或缩小。
C.化合物Ⅳ的制备:
在50毫升单口圆底烧瓶中加入2.45毫摩尔化合物Ⅲ,用15毫升二氯甲烷溶解,在冰浴条件下向反应中加入2.37克,即14.68毫摩尔二乙氨基三氟化硫,加完之后室温搅拌12小时,反应结束后将反应液倒入冰水中,加入碳酸钠直至混合物不产生气泡。然后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为5:1,收率65-75%;化合物Ⅳ制备的量和反应容器的体积按相应比例扩大或缩小。
D.化合物Ⅴ的制备:
在50毫升单口圆底烧瓶中加入4.02毫摩尔化合物Ⅳ,用10毫升乙醇溶解,再向反应中加入0.32克,即8.04毫摩尔氢氧化钠,加完之后60℃搅拌1.5小时,反应完全后减压除去溶剂,残余物用10mL水稀释,加入2mol/L稀盐酸调节pH至2-3。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。蒸发溶剂得化合物Ⅴ,收率90-95%,化合物Ⅴ制备的量和反应容器的体积按相应比例扩大或缩小。
E.化合物Ⅵ的制备:
在50毫升单口圆底烧瓶中加入4.56毫摩尔化合物Ⅴ,再加入5mL二氯亚砜,加完之后80℃搅拌2小时,反应完全后减压除去溶剂,得化合物Ⅵ,无需进一步纯化即可用于下一步反应,化合物Ⅵ制备的量和反应容器的体积按相应比例扩大或缩小。
F.化合物Ⅷ的制备:
在50毫升单口圆底烧瓶中加入0.65毫摩尔化合物Ⅶ,用5毫升二氯甲烷溶解,向反应中加入0.72毫摩尔三乙胺,加完之后室温搅拌15分钟。然后加入0.65毫摩尔化合物Ⅵ的二氯甲烷溶液,加完之后室温搅拌5小时。反应完全后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率31-94%,化合物Ⅷ制备的量和反应容器的体积按相应比例扩大或缩小。
G.本发明的吡唑酰胺衍生物Ⅷ的杀菌活性测定:
本发明的吡唑酰胺衍生物Ⅷ的杀菌或抑菌活性采用菌体生长率测定法,具体步骤为:取1毫克样品溶解在50微升N,N-二甲基甲酰胺中,然后用含有一定量吐温80乳化剂的水溶液稀释至1000微克/毫升的药剂,将供试药剂在无菌条件下各吸取1毫升于培养皿内,再分别加入9毫升PDA培养基,摇匀后制成100微克/毫升含药平板,以添加1毫升灭菌水的平板做空白对照,用直径6毫米的打孔器沿菌丝外缘切取菌盘,移至含药平板上,呈等边三角形摆放,每处理重复3次,将培养皿放在24±1摄氏度恒温培养箱内培养,待对照菌落直径扩展到2-3厘米后调查各处理菌盘扩展直径,求平均值,与空白对照比较计算相对抑菌率,供试菌种为我国农业生产中田间实际发生的大部分典型植物病原菌的种属,其代号和名称如下:PA:瓜果腐霉病菌,其拉丁名为:Pythium aphanidermatum、FO:茄子枯萎病菌,其拉丁名为:Fusarium oxysporum、PP:苹果轮纹病菌,其拉丁名为:Physalospora piricola、FG:玉米穗腐病菌,其拉丁名为:Fusarium graminearum、RC:禾谷丝核菌,其拉丁名为:Rhizoctonia cerealis、SS:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum、RS:立枯丝核病菌,其拉丁名为:Rhizoctonia solani、AS:番茄早疫病菌,其拉丁名为:Alternaria solani、GZ:小麦赤霉病菌,其拉丁名为:Gibberella zeae、BC:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、CA:花生褐斑病菌,其拉丁名为:Cercosporaarachidicola。
H.本发明的吡唑酰胺衍生物Ⅷ诱导抗病活性的测定:
吡唑酰胺衍生物Ⅷ的活性筛选方法如下:
(1).阳性对照植物免疫诱导活性化合物:选择质量纯度纯度大于99.5%的CMPA为阳性对照的植物植物免疫诱导活性化合物。
(2).吡唑酰胺衍生物Ⅷ诱导黄瓜抗病活性的测定方法:采用Q-PCR法对诱导抗病基因的表达量进行测定。处理方式包括:喷施浓度为100微克/毫升供试化合物溶液2到3次,每次10毫升,每处理重复三次,空白对照和标准药剂对照分别选择水和CMPA,将黄瓜苗置于其生长适宜温度及光照下培养。最后一次处理24h后,收集处理过的黄瓜叶片,用植物RNA试剂盒分离RNA;mRNA用cDNA试剂盒逆转录,Q-PCR使用2-ΔΔCt方法进行:
R=2-ΔΔCt
其中,R为供试化合物对黄瓜抗病基因的诱导效果;ΔΔCt=ΔCt(试验样品)-ΔCt(基准样品);ΔCt(试验样品)=Ct(试验样品,目的基因)-Ct(试验样品,内参基因),ΔCt(基准样品)=Ct(基准样品,目的基因)-Ct(基准样品,内参基因)。
采用酶活法对植物防御反应相关的关键酶苯丙氨酸解氨酶(PAL)活性进行测定。处理方式包括:喷施浓度为100微克/毫升供试化合物溶液2到3次,每次10毫升,每处理重复三次,空白对照和标准药剂对照分别选择水和CMPA,将黄瓜苗置于其生长适宜温度及光照下培养。最后一次处理24h后,收集处理过的黄瓜叶片,用试剂盒测定PAL活性:
X=17.3×ΔA÷W
其中,X为供试化合物对黄瓜防御反应相关的PAL酶活性诱导效果,单位:U/g;ΔA为290nm处测定管吸光值和空白管吸光值的差值;W为样本质量,单位:g。
本发明的有益效是:对吡唑酰胺衍生物Ⅷ进行了先导优化,并对吡唑酰胺衍生物Ⅷ进行了抑菌活性的筛选。
本发明通过特定制备和生物活性测定实施例更加具体说明吡唑酰胺衍生物Ⅷ的合成与生物活性及应用,所述实施例仅用于具体说明本发明而非限制本发明,尤其是生物活性仅是举例说明,而非限制本专利,具体实施方式如下:
实施例1:化合物Ⅱ的制备方法:
在100毫升单口圆底烧瓶中加入33.38毫摩尔化合物I和41.73毫摩尔甲基肼硫酸盐,加入12毫升甲苯和12毫升冰乙酸溶解,再加入83.45毫摩尔乙酸钠,100℃搅拌1.5小时,反应完全后减压除去溶剂,残余物经100~200目硅胶柱层析纯化得化合物Ⅱ,洗脱剂为二氯甲烷:乙酸乙酯,体积比为5:1,收率85-95%;化合物Ⅱ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例2:化合物III的制备方法:
在100毫升单口圆底烧瓶中加入8.29毫摩尔化合物Ⅱ和33.16毫摩尔N,N-二甲基甲酰胺溶液,再向反应中加入66.32毫摩尔三氯氧磷,然后90℃加热回流3小时,反应结束后将反应液倒入冰水中,加入碳酸氢钠直至混合物不产生气泡。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤,减压除去溶剂,残余物经100~200目硅胶柱层析纯化得到白色固体,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率80-90%;化合物Ⅲ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例3:化合物Ⅳ的制备方法:
在50毫升单口圆底烧瓶中加入2.45毫摩尔化合物Ⅲ,用15毫升二氯甲烷溶解,在冰浴条件下向反应中加入2.37克,即14.68毫摩尔二乙氨基三氟化硫,加完之后室温搅拌12小时,反应结束后将反应液倒入冰水中,加入碳酸钠直至混合物不产生气泡。然后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为5:1,收率65-75%;化合物Ⅳ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例4:化合物Ⅴ的制备方法:
在50毫升单口圆底烧瓶中加入4.02毫摩尔化合物Ⅳ,用10毫升乙醇溶解,再向反应中加入0.32克,即8.04毫摩尔氢氧化钠,加完之后60℃搅拌1.5小时,反应完全后减压除去溶剂,残余物用10mL水稀释,加入2mol/L稀盐酸调节pH至2-3。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。蒸发溶剂得化合物Ⅴ,收率90-95%,化合物Ⅴ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例5:化合物Ⅵ的制备方法:
在50毫升单口圆底烧瓶中加入4.56毫摩尔化合物Ⅴ,再加入5mL二氯亚砜,加完之后80℃搅拌2小时,反应完全后减压除去溶剂,得化合物Ⅵ,无需进一步纯化即可用于下一步反应,化合物Ⅵ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例6:化合物Ⅷ的制备方法:
在50毫升单口圆底烧瓶中加入0.65毫摩尔化合物Ⅶ,用5毫升二氯甲烷溶解,向反应中加入0.72毫摩尔三乙胺,加完之后室温搅拌15分钟。然后加入0.65毫摩尔化合物Ⅵ的二氯甲烷溶液,加完之后室温搅拌5小时。反应完全后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率31-94%,化合物Ⅷ制备的量和反应容器的体积按相应比例扩大或缩小。
实施例7:化合物S26的制备方法:
在50毫升单口圆底烧瓶中加入0.65毫摩尔化合物Ⅶ,用5毫升二氯甲烷溶解,向反应中加入0.72毫摩尔三乙胺,加完之后室温搅拌15分钟。然后加入0.65毫摩尔化合物Ⅵ的二氯甲烷溶液,加完之后室温搅拌5小时。反应完全后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率70%,化合物Ⅷ的理化参数和结构参数见表1。
实施例8:本发明的吡唑酰胺衍生物Ⅷ的抑菌活性测定结果:
本发明测试的常见植物病原真菌的代号和名称如下:PA:瓜果腐霉病菌,其拉丁名为:Pythium aphanidermatum、FO:茄子枯萎病菌,其拉丁名为:Fusarium oxysporum、PP:苹果轮纹病菌,其拉丁名为:Physalospora piricola、FG:玉米穗腐病菌,其拉丁名为:Fusarium graminearum、RC:禾谷丝核菌,其拉丁名为:Rhizoctonia cerealis、SS:油菜菌核病菌,其拉丁名为:Sclerotinia sclerotiorum、RS:立枯丝核病菌,其拉丁名为:Rhizoctonia solani、AS:番茄早疫病菌,其拉丁名为:Alternaria solani、GZ:小麦赤霉病菌,其拉丁名为:Gibberella zeae、BC:黄瓜灰霉病菌,其拉丁名为:Botrytis cinerea、CA:花生褐斑病菌,其拉丁名为:Cercospora arachidicola,这些菌种具有很好的代表性,能够代表农业生产中田间发生的大部分病原菌的种属。
菌体生长率法测定结果见表2,表2表明,在100微克/毫升时,本发明合成的吡唑酰胺类所有化合物均有不同程度的杀菌活性。对于瓜果腐霉病菌,化合物S3、S4、S7、S8、S12、S15、S20、S21、S22、S24、S25、S26、S27、S28、S30的抑制率均在20%以上,上述化合物的杀菌活性均高于对照药啶酰菌胺和吡唑萘菌胺,其中化合物S26的抑制率最高,在50%以上,高出对照药啶酰菌胺40%以上和对照药吡唑萘菌胺30%以上;对于茄子枯萎病菌,化合物S2、S4、S6、S9、S10、S11、S12、S25、S26、S27、S28的抑制率均在25%以上,上述化合物的杀菌活性均高于对照药啶酰菌胺和吡唑萘菌胺,其中化合物S4、S26的抑菌率均在50%以上,均高出对照药啶酰菌胺45%以上和对照药吡唑萘菌胺30%以上,尤其是化合物S26杀菌活性最高,达56%;对于苹果轮纹病菌,化合物S2、S4、S5、S6、S7、S8、S9、S10、S11、S12、S16、S19、S25、S26、S27的抑制率均在30%以上,上述化合物的杀菌活性均高于对照药啶酰菌胺,其中化合物S19、S26的抑菌率均在45%以上,均高出对照药啶酰菌胺15%以上,尤其是化合物S26杀菌活性最高,达52%;对于玉米穗腐病菌,化合物S2、S4、S5、S7、S10、S11、S16、S22、S23、S24、S26、S27、S29、S30的抑制率均在20%以上,上述化合物的杀菌活性均高于对照药啶酰菌胺,其中化合物S26、S27的抑菌率均在50%以上,均高出对照药啶酰菌胺35%以上和对照药吡唑萘菌胺20%以上,尤其是化合物S27杀菌活性最高,达54%;对于禾谷丝核菌,化合物S14、S15、S18、S22、S24、S26、S27、S28、S30的抑制率均在60%以上,其中化合物S24、S26的抑制率均在80%以上,高于对照药啶酰菌胺;对于油菜菌核病菌,化合物S2、S9、S15、S17、S24、S26的抑制率均在30%以上,其中化合物S2、S26的抑制率均在40%以上,均高于对照药啶酰菌胺和对照药吡唑萘菌胺;对于立枯丝核病菌,化合物S3、S4、S5、S7、S10、S11、S20、S22、S26、S27、S29的抑制率均在40%以上,此外化合物S22、S26、S27的抑制率均在60%以上,其中化合物S26的抑制率最高,为70%;对于番茄早疫病菌,化合物S1、S2、S4、S6、S10、S11、S12、S13、S19、S20、S22、S23、S26、S27、S28、S30的抑制率均在50%以上,此外化合物S4、S11、S13、S26的抑制率均在60%以上,高于对照药啶酰菌胺,其中化合物S26的抑制率最高,为88%,接近对照药吡唑萘菌胺;对于小麦赤霉病菌,化合物S1、S2、S3、S4、S5、S6、S7、S8、S10、S11、S12、S14、S15、S16、S17、S18、S24、S25、S26、S27、S28、S30的抑制率均在30%以上,均高于对照药啶酰菌胺和对照药吡唑萘菌胺,此外化合物S1、S4、S8、S12、S26、S27、S28的抑制率在50%以上,均高于对照药啶酰菌胺30%以上和对照药吡唑萘菌胺20%以上,其中化合物S1抑制率最高,为69%;对于黄瓜灰霉病菌,化合物S1、S2、S3、S4、S5、S6、S7、S8、S10、S11、S12、S16、S24、S26、S28的抑制率均在60%以上,此外化合物S3、S5、S7、S26、S28的抑制率在80%以上,均高于对照药吡唑萘菌胺,化合物S5、S7、S26的抑制率在85%以上,均高于对照药啶酰菌胺,其中化合物S7的抑制率最高,为96%;对于花生褐斑病菌,化合物S3、S16、S20、S22、S26、S27、S28、S30的抑制率均在30%以上,均高于对照药啶酰菌胺和对照药吡唑萘菌胺,此外化合物S26、S28抑制率均在70%以上,均高于对照药啶酰菌胺60%以上和对照药吡唑萘菌胺45%以上,其中化合物S26的抑制率最高,为86%;综上可见,化合物S26具有广谱的杀菌活性。
实施例9:本发明的吡唑酰胺衍生物Ⅷ防治黄瓜灰霉病的温室盆栽试验结果:
本发明吡唑酰胺衍生物Ⅷ开展了温室盆栽试验,选择的防治对象的名称及代号如下:灰霉病(Botrytis cinerea);选择的试验作物品种为“长春密刺”的黄瓜。处理方式:待黄瓜长到三叶期,喷洒100μg/mL的吡唑酰胺衍生物Ⅷ,对照植株喷洒不含任何测试化合物的空白溶液,24小时后接种黄瓜灰霉病菌,在25℃培养6天后调查结果。实验结果见表3,表3表明,化合物S1、S2、S3、S11、S12、S26、S28对黄瓜灰霉病菌的抑制率在45%以上,其中化合物S3、S12、S26对黄瓜灰霉病菌的抑制率在80%以上,化合物S3、S12对黄瓜灰霉病菌的抑制率与对照药剂啶酰菌胺和对照药剂吡唑萘菌胺相当,化合物S6对黄瓜灰霉病菌的抑制率优于对照药剂啶酰菌胺和对照药剂吡唑萘菌胺相当。综上所述:化合物S26对黄瓜灰霉病有较好的防治效果。
实施例10:本发明的吡唑酰胺衍生物Ⅷ的诱导抗病活性结果:
吡唑酰胺衍生物Ⅷ对植物防御相关基因的诱导效果见表4,表4表明,本发明的吡唑酰胺衍生物S26具有较好的诱导抗病活性;在100微克/毫升时S26对RBOH基因的诱导效果是空白的10.321倍,接近阳性对照植物激活剂CMPA的2倍;S26对WRKY30基因的诱导效果是空白的2.586倍,与阳性对照植物激活剂CMPA相当;S26对WRKY6基因的诱导效果是空白的6.444倍,是阳性对照植物激活剂CMPA的2倍以上;S26对PR1基因的诱导效果是空白的22.013倍,是阳性对照植物激活剂CMPA的3倍以上;S26对PAL基因的诱导效果是空白的2.921倍,优于阳性对照植物免疫诱导活性化合物CMPA;综上所述,本发明的吡唑酰胺衍生物Ⅷ对植物防御相关基因具有较好的诱导效果。
吡唑酰胺衍生物Ⅷ对植物防御反应相关的关键酶苯丙氨酸解氨酶(PAL)的诱导效果见表5,表5表明,本发明的吡唑酰胺衍生物Ⅷ对PAL具有较好的诱导效果;用100微克/毫升的S3处理后PAL的酶活是19.145,优于对照药剂啶酰菌胺,接近阳性对照植物免疫诱导活性化合物CMPA;用100微克/毫升的S12处理后PAL的酶活是24.655,优于对照药剂啶酰菌胺和阳性植物免疫诱导活性化合物CMPA;用100微克/毫升的S26处理后PAL的酶活是34.416,是对照药剂啶酰菌胺的2倍以上,是阳性对照药植物免疫诱导活性化合物CMPA的1.5倍以上;综上所述,本发明的吡唑酰胺衍生物Ⅷ对植物防御反应相关的关键酶PAL具有较好的诱导效果,因此本发明的吡唑酰胺衍生物Ⅷ具有较好的诱导抗病活性。
实施例11:本发明的吡唑酰胺衍生物Ⅷ与杀虫剂组合在防治农业和林业以及园艺植物虫害中的应用:
本发明的所有吡唑酰胺衍生物Ⅷ与商品杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害,所述商品杀虫剂选自:毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲,其CAS号为121451-02-3、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即{1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲}、Bay SIR-8514即[1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲]、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、三唑磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、三唑锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素;本发明的吡唑酰胺衍生物Ⅷ在所述杀虫组合物中的质量百分含量是1%-90%,本发明的吡唑酰胺衍生物Ⅷ与前述商品杀虫剂的比例为质量百分比1%:99%到99%:1%;所述杀虫组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀虫组合物防治的植物虫害选自:红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫;所述杀虫组合物防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例12:本发明的吡唑酰胺衍生物Ⅷ与杀菌剂组合在防治农业和林业以及园艺植物病害中的应用:
本发明的所有吡唑酰胺衍生物Ⅷ与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害,所述商品杀菌剂选自:苯并噻二唑、噻酰菌胺,简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺,其英文通用名为:isotianil、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑;本发明的吡唑酰胺衍生物Ⅷ在所述杀菌组合物中的总的质量百分含量是1%-90%,本发明的吡唑酰胺衍生物Ⅷ与前述商品杀菌剂的比例为质量百分比1%:99%到99%:1%;所述杀菌组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀菌组合物防治的植物病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病;所述杀菌组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例13:本发明的吡唑酰胺衍生物Ⅷ与抗植物病毒剂组合在防治农业和林业以及园艺植物病毒病害中的应用:
本发明的所有吡唑酰胺衍生物Ⅷ与商品抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害,所述商品抗病毒药剂选自:苯并噻二唑、噻酰菌胺,简写为TDL、异噻菌胺,其英文通用名为:isotianil、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素;本发明的吡唑酰胺衍生物Ⅷ在所述抗病毒组合物中的总的质量百分含量是1%-90%,本发明的吡唑酰胺衍生物Ⅷ与前述商品抗植物病毒剂的比例为质量百分比1%:99%到99%:1%;所述抗病毒组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述抗病毒组合物防治的病毒病害选自:水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;所述抗病毒组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
实施例14:本发明的吡唑酰胺衍生物Ⅷ与杀螨剂组合在防治农业和林业以及园艺植物螨害中的应用:
本发明的所有吡唑酰胺衍生物Ⅷ与商品杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害,所述商品杀螨剂选自:三唑锡、三环锡、苯丁锡、三磷锡、毒虫畏、甲基毒虫畏、巴毒磷、敌敌畏、庚烯磷、速灭磷、久效磷、二溴磷、毒死蜱、嘧啶磷、氯甲亚胺硫磷、氧乐果、敌杀磷、乙硫磷、马拉硫磷、虫螨畏、伏杀硫磷、辛硫磷、甲基嘧啶硫磷、喹硫磷、治螟磷、三唑磷、蚜灭多、水胺硫磷、甲胺磷、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、涕灭威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、克百威、丁硫克百威、速灭威、蜱虱威、伐虫脒、单甲脒、杀螨脒、双甲脒、杀虫脒、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵;本发明的吡唑酰胺衍生物Ⅷ在所述杀螨组合物中的总的质量百分含量是1%-90%,本发明的吡唑酰胺衍生物Ⅷ与所述商品杀螨剂的比例为质量百分比1%:99%到99%:1%;所述杀螨组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀螨组合物防治的螨害选自:螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨,这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨;所述杀螨组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
表1本发明的吡唑酰胺衍生物Ⅷ的化学结构和理化参数
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表2本发明的吡唑酰胺衍生物Ⅷ的抑菌活性(100微克/毫升的抑制率/%)
序号 | 化合物 | P.a | F.o | P.p | F.g | R.c | S.s | R.s | A.s | G.z | B.c | C.a |
1 | S1 | 0 | 11±1 | 15±1 | 0 | 35±2 | 0 | 28±2 | 59±1 | 69±2 | 68±2 | 12±1 |
2 | S2 | 18±1 | 43±1 | 34±1 | 26±2 | 35±1 | 43±1 | 19±1 | 59±1 | 36±2 | 64±1 | 16±2 |
3 | S3 | 23±1 | 20±1 | 27±2 | 11±1 | 45±1 | 10±1 | 42±1 | 37±1 | 46±2 | 83±1 | 31±0 |
4 | S4 | 25±2 | 55±2 | 39±1 | 22±2 | 51±1 | 27±1 | 53±2 | 65±2 | 53±2 | 74±2 | 12±1 |
5 | S5 | 18±1 | 19±2 | 37±0 | 24±1 | 53±2 | 29±1 | 49±1 | 43±1 | 51±1 | 89±2 | 29±2 |
6 | S6 | 19±1 | 30±1 | 36±1 | 20±1 | 37±1 | 20±2 | 34±1 | 57±2 | 39±2 | 68±2 | 20±1 |
7 | S7 | 23±1 | 19±1 | 33±2 | 24±1 | 31±2 | 24±1 | 44±1 | 49±1 | 51±2 | 96±1 | 16±1 |
8 | S8 | 21±1 | 19±1 | 36±2 | 19±1 | 31±1 | 25±1 | 38±2 | 49±2 | 55±2 | 64±1 | 20±1 |
9 | S9 | 19±2 | 40±1 | 31±2 | 17±1 | 31±1 | 31±1 | 37±1 | 46±2 | 29±1 | 30±1 | 22±1 |
10 | S10 | 16±2 | 26±1 | 40±2 | 31±2 | 34±2 | 25±1 | 41±2 | 51±2 | 48±1 | 77±2 | 16±1 |
11 | S11 | 18±2 | 26±1 | 33±1 | 22±1 | 38±1 | 27±1 | 44±2 | 65±2 | 48±2 | 66±1 | 16±1 |
12 | S12 | 21±1 | 34±1 | 37±1 | 17±1 | 25±1 | 18±2 | 37±1 | 59±2 | 55±1 | 68±2 | 20±1 |
13 | S13 | 20±1 | 6±2 | 3±1 | 9±1 | 43±1 | 8±2 | 6±1 | 70±2 | 17±1 | 42±1 | 12±1 |
14 | S14 | 16±1 | 11±1 | 11±2 | 13±2 | 75±0 | 24±1 | 14±1 | 40±1 | 41±2 | 27±0 | 11±1 |
15 | S15 | 21±1 | 17±1 | 8±1 | 20±1 | 76±0 | 30±1 | 24±1 | 37±1 | 40±2 | 37±1 | 8±1 |
16 | S16 | 18±1 | 15±1 | 35±2 | 22±1 | 43±1 | 17±1 | 34±1 | 37±1 | 39±1 | 77±2 | 31±1 |
17 | S17 | 16±1 | 11±1 | 8±2 | 20±2 | 57±1 | 35±2 | 5±1 | 43±2 | 39±2 | 46±1 | 14±1 |
18 | S18 | 16±1 | 16±1 | 14±2 | 17±1 | 64±1 | 28±1 | 14±1 | 37±2 | 38±2 | 32±1 | 14±1 |
19 | S19 | 19±1 | 13±2 | 45±1 | 9±1 | 47±1 | 5±2 | 40±0 | 51±2 | 0 | 17±1 | 23±1 |
20 | S20 | 26±1 | 25±1 | 24±1 | 15±1 | 42±1 | 18±1 | 44±1 | 58±2 | 6±1 | 59±1 | 30±1 |
21 | S21 | 26±1 | 15±1 | 26±0 | 9±1 | 49±0 | 16±1 | 22±1 | 47±2 | 0 | 39±1 | 23±1 |
22 | S22 | 25±1 | 18±1 | 29±1 | 26±1 | 62±1 | 13±2 | 63±2 | 55±1 | 32±1 | 27±1 | 43±1 |
23 | S23 | 19±1 | 7±1 | 24±2 | 23±1 | 42±1 | 3±1 | 36±1 | 60±1 | 15±2 | 39±1 | 23±1 |
24 | S24 | 21±1 | 22±1 | 14±1 | 25±2 | 81±2 | 31±1 | 12±1 | 34±2 | 40±2 | 70±2 | 19±1 |
25 | S25 | 25±1 | 27±2 | 33±1 | 4±1 | 41±1 | 10±1 | 32±1 | 40±1 | 41±1 | 55±1 | 19±1 |
26 | S26 | 53±2 | 56±2 | 52±1 | 50±0 | 81±2 | 52±0 | 70±1 | 88±2 | 66±1 | 92±1 | 86±1 |
27 | S27 | 32±1 | 32±1 | 39±1 | 54±1 | 72±1 | 24±1 | 64±1 | 54±2 | 55±1 | 60±1 | 37±1 |
28 | S28 | 33±1 | 25±2 | 15±1 | 13±1 | 60±1 | 13±2 | 29±0 | 52±0 | 57±2 | 85±2 | 74±2 |
29 | S29 | 14±1 | 16±2 | 14±1 | 24±0 | 51±1 | 24±1 | 51±2 | 29±1 | 6±1 | 47±1 | 13±1 |
30 | S30 | 30±2 | 19±1 | 15±1 | 22±1 | 60±1 | 23±0 | 34±2 | 55±1 | 41±2 | 45±1 | 52±1 |
31 | boscalid | 12±2 | 7±1 | 29±0 | 15±1 | 77±0 | 37±1 | 77±1 | 64±1 | 21±2 | 87±1 | 13±1 |
32 | isopyrazam | 20±1 | 24±1 | 64±0 | 27±2 | 100 | 33±2 | 100 | 89±1 | 32±2 | 78±1 | 26±2 |
表3本发明的吡唑酰胺衍生物Ⅷ防治黄瓜灰霉病的活性(100微克/毫升的抑制率/%)
表4本发明的吡唑酰胺衍生物Ⅷ对防御相关基因的诱导效果(100微克/毫升的诱导效果/倍)
表5本发明的吡唑酰胺衍生物Ⅷ对PAL酶的诱导效果(100微克/毫升的酶活/U/g)
化合物 | 质量(g) | ΔA(U) | 酶活(U/g) |
CK | 0.4769 | 0.464 | 16.832 |
啶酰菌胺 | 0.4383 | 0.396 | 15.630 |
CMPA | 0.3870 | 0.501 | 22.396 |
S3 | 0.4238 | 0.469 | 19.145 |
S12 | 0.4996 | 0.712 | 24.655 |
S26 | 0.5087 | 1.012 | 34.416 |
Claims (8)
1.一类吡唑-3-甲酰胺衍生物,其特征在于具有如式Ⅷ所示的化学结构通式:
Ⅷ:
其中,R选自:2-氟苯基,2-氯苯基,3-异丙氧基苯基,4-(三氟甲氧基)苯基,3-硝基苯酚-4-基,(1,1-联苯)-2-基,4-乙烯基-(1,1-联苯)-2-基,4-甲氧基-(1,1-联苯)-2-基,4-氟-(1,1-联苯)-2-基,3,4-二氟-(1,1-联苯)-2-基,4-甲基-3-氯-(1,1-联苯)-2-基,4-甲基-3,5-二氟-(1,1-联苯)-2-基,2-苯基吡啶-3-基,2-苯基吡啶-4-基,2-(4-甲氧基苯基)吡啶-5-基,2-苯氧基苯基,2-(邻甲苯氧基)苯基,5-氯-2-苯氧基苯基,5-氯-2-(4-氯苯氧基)苯基,2-(4-氯苯氧基)苯基,4-(4-甲氧基苯氧基)苯基,1-甲基-4-苯氧基苯基,3-苄氧基苯基,4-((5-(三氟甲基)吡啶-2-基)氧基)苯基,4-氟-2-(苯基氨基)苯基,4-氟-2-((4-(叔丁基)苯基)氨基)苯基,4-氟-2-((3-氟苯基)氨基)苯基,4-氟-2-((3-氟-2-甲氧基苯基)氨基)苯基,4-氟-2-((3-氟-4-甲基苯基)氨基)苯基,4-氟-2-((3,4-二氟苯基)氨基)苯基。
2.权利要求1所述的唑酰胺类衍生物Ⅷ的合成方法,具体合成路线如下:
其中,R选自:2-氟苯基,2-氯苯基,3-异丙氧基苯基,4-(三氟甲氧基)苯基,3-硝基苯酚-4-基,(1,1-联苯)-2-基,4-乙烯基-(1,1-联苯)-2-基,4-甲氧基-(1,1-联苯)-2-基,4-氟-(1,1-联苯)-2-基,3,4-二氟-(1,1-联苯)-2-基,4-甲基-3-氯-(1,1-联苯)-2-基,4-甲基-3,5-二氟-(1,1-联苯)-2-基,2-苯基吡啶-3-基,2-苯基吡啶-4-基,2-(4-甲氧基苯基)吡啶-5-基,2-苯氧基苯基,2-(邻甲苯氧基)苯基,5-氯-2-苯氧基苯基,5-氯-2-(4-氯苯氧基)苯基,2-(4-氯苯氧基)苯基,4-(4-甲氧基苯氧基)苯基,1-甲基-4-苯氧基苯基,3-苄氧基苯基,4-((5-(三氟甲基)吡啶-2-基)氧基)苯基,4-氟-2-(苯基氨基)苯基,4-氟-2-((4-(叔丁基)苯基)氨基)苯基,4-氟-2-((3-氟苯基)氨基)苯基,4-氟-2-((3-氟-2-甲氧基苯基)氨基)苯基,4-氟-2-((3-氟-4-甲基苯基)氨基)苯基,4-氟-2-((3,4-二氟苯基)氨基)苯基。
权利要求1所述的唑酰胺类衍生物的合成具体方法分为以下步骤:
A.化合物Ⅱ的制备方法:
在100毫升单口圆底烧瓶中加入33.38毫摩尔化合物I和41.73毫摩尔甲基肼硫酸盐,加入12毫升甲苯和12毫升冰乙酸溶解,再加入83.45毫摩尔乙酸钠,100℃搅拌1.5小时,反应完全后减压除去溶剂,残余物经100~200目硅胶柱层析纯化得化合物Ⅱ,洗脱剂为二氯甲烷:乙酸乙酯,体积比为5:1,收率85-95%;化合物Ⅱ制备的量和反应容器的体积按相应比例扩大或缩小;
B.化合物III的制备方法:
在100毫升单口圆底烧瓶中加入8.29毫摩尔化合物Ⅱ和33.16毫摩尔N,N-二甲基甲酰胺溶液,再向反应中加入66.32毫摩尔三氯氧磷,然后90℃加热回流3小时,反应结束后将反应液倒入冰水中,加入碳酸氢钠直至混合物不产生气泡。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤,减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率80-90%;化合物Ⅲ制备的量和反应容器的体积按相应比例扩大或缩小;
C.化合物Ⅳ的制备方法:
在50毫升单口圆底烧瓶中加入2.45毫摩尔化合物Ⅲ,用15毫升二氯甲烷溶解,在冰浴条件下向反应中加入2.37克,即14.68毫摩尔二乙氨基三氟化硫,加完之后室温搅拌12小时,反应结束后将反应液倒入冰水中,加入碳酸钠直至混合物不产生气泡。然后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,抽滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为5:1,收率65-75%;化合物Ⅳ制备的量和反应容器的体积按相应比例扩大或缩小;
D.化合物Ⅴ的制备方法:
在50毫升单口圆底烧瓶中加入4.02毫摩尔化合物Ⅳ,用10毫升乙醇溶解,再向反应中加入0.32克,即8.04毫摩尔氢氧化钠,加完之后60℃搅拌1.5小时,反应完全后减压除去溶剂,残余物用10mL水稀释,加入2mol/L稀盐酸调节pH至2-3。然后用乙酸乙酯萃取,水层用乙酸乙酯反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。蒸发溶剂得化合物Ⅴ,收率90-95%,化合物Ⅴ制备的量和反应容器的体积按相应比例扩大或缩小。
E.化合物Ⅵ的制备方法:
在50毫升单口圆底烧瓶中加入4.56毫摩尔化合物Ⅴ,再加入5mL二氯亚砜,加完之后80℃搅拌2小时,反应完全后减压除去溶剂,得化合物Ⅵ,无需进一步纯化即可用于下一步反应,化合物Ⅵ制备的量和反应容器的体积按相应比例扩大或缩小;
F.化合物Ⅷ的制备方法:
在50毫升单口圆底烧瓶中加入0.65毫摩尔化合物Ⅶ,用5毫升二氯甲烷溶解,向反应中加入0.72毫摩尔三乙胺,加完之后室温搅拌15分钟。然后加入0.65毫摩尔化合物Ⅵ的二氯甲烷溶液,加完之后室温搅拌5小时。反应完全后用二氯甲烷萃取,水层用二氯甲烷反萃一遍,合并有机层,有机层用饱和氯化钠洗一遍,无水硫酸钠干燥,过滤。减压除去溶剂,残余物经100~200目硅胶柱层析纯化,洗脱剂为60~90摄氏度的石油醚:乙酸乙酯,体积比为3:1,收率31-94%,化合物Ⅷ制备的量和反应容器的体积按相应比例扩大或缩小。
3.权利要求1所述的吡唑酰胺衍生物Ⅷ与农业上可接受的助剂在制备杀菌剂中的用途。
4.权利要求1所述的吡唑酰胺衍生物Ⅷ与农业上可接受的助剂在制备植物免疫诱导剂中的用途。
5.权利要求1所述的吡唑酰胺衍生物Ⅷ与杀虫剂组合在防治农业和林业以及园艺植物虫害中的用途:
权利要求1所述的吡唑酰胺衍生物Ⅷ与商品杀虫剂中的任意一种或两种组合形成杀虫组合物用于防治农业和林业以及园艺植物虫害,所述商品杀虫剂选自:毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲,其CAS号为121451-02-3、氟螨脲、Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲、Bay SIR-8514即1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、三唑磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、三唑锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素;权利要求1所述的吡唑酰胺衍生物Ⅷ在所述杀虫组合物中的质量百分含量是1%-90%,权利要求1所述的吡唑酰胺衍生物Ⅷ与前述商品杀虫剂的比例为质量百分比1%∶99%到99%∶1%;所述杀虫组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀虫组合物防治的植物虫害选自:红蜘蛛、东亚飞蝗、云斑车蝗、中华稻蝗、日本黄脊蝗、单刺蝼蛄、东方蝼蛄、稻蓟马、烟蓟马、温室蓟马、稻管蓟马、麦简管蓟马、温室白粉虱、烟粉虱、黑尾叶蝉、大青叶蝉、棉叶蝉、斑衣蜡蝉、褐飞虱、白背飞虱、灰飞虱、甘蔗扁角飞虱、棉蚜、麦二叉蚜、麦长管蚜、桃蚜、高粱蚜、萝卜蚜、吹绵蚧、桑盾蚧、矢尖盾蚧、梨圆蚧、白蜡虫、红蜡蚧、朝鲜球坚蚧、梨网蝽、香蕉网蝽、细角花蝽、微小花蝽、针缘蝽、稻蛛缘蝽、稻褐蝽、稻黑蝽、稻绿蝽、绿盲蝽、苜蓿盲蝽、中黑盲蝽、大草蛉、丽草蛉、中华草蛉、谷蛾、衣蛾、黄刺蛾、褐刺蛾、扁刺蛾、麦蛾、棉红铃虫、甘薯麦蛾、小菜蛾、桃小食心虫、大豆食心虫、桃小食心虫、苹果顶梢卷叶蛾、褐带长卷叶蛾、拟小黄卷叶蛾、二化螟、豆荚螟、玉米螟、三化螟、菜螟、稻纵卷叶螟、条螟、棉卷叶野螟、桃蛀螟、黏虫、斜纹夜蛾、稻螟蛉、棉小造桥虫、甜菜夜蛾、大螟、棉铃虫、鼎点金刚钻、小地老虎、大地老虎、黄地老虎、盗毒蛾、舞毒蛾、甘薯天蛾、豆天蛾、直纹稻弄蝶、隐纹谷弄蝶、柑橘凤蝶、玉带凤蝶、菜粉蝶、苎麻赤蛱蝶、苎麻黄蛱蝶、豆芫菁、金星步甲、皱鞘步甲、麦穗步甲、沟金针虫、细胸金针虫、谷斑皮蠹、黑皮蠹、柑橘小吉丁虫、金缘吉丁虫、黄粉虫、黑粉虫、赤拟谷盗、杂拟谷盗、铜绿异丽金龟、暗黑金龟、华北大黑鳃金龟、桑天牛、星天牛、橘褐天牛、桃红颈天牛、大猿叶虫、小猿叶虫、黄守瓜、黄曲条跳甲、绿豆象、豌豆象、蚕豆象、玉米象、米象、小麦叶蜂、梨实蜂、黄带姬蜂、黏虫白星姬蜂、螟蛉悬茧姬蜂、棉铃虫齿唇姬蜂、螟黑点疣姬蜂、蚊、蝇、虻、麦红吸浆虫、麦黄吸浆虫、稻瘿蚊、柑橘大实蝇、瓜实蝇、麦叶灰潜蝇、美洲斑潜蝇、豆秆黑潜蝇、麦秆蝇、种蝇、葱蝇、萝卜蝇、伞裙追寄蝇、玉米螟厉寄蝇、黏虫;所述杀虫组合物防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
6.权利要求1所述的吡唑酰胺衍生物Ⅷ与杀菌剂组合在防治农业和林业以及园艺植物病害中的用途:
权利要求1所述的吡唑酰胺衍生物Ⅷ与商品杀菌剂中的任意一种或两种组合形成杀菌组合物用于防治农业和林业以及园艺植物病害,所述商品杀菌剂选自:苯并噻二唑、噻酰菌胺,简写为TDL、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺,其英文通用名为:isotianil、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑;权利要求1所述的吡唑酰胺衍生物Ⅷ在所述杀菌组合物中的总的质量百分含量是1%-90%,权利要求1所述的异吡唑酰胺衍生物Ⅷ与前述商品杀菌剂的比例为质量百分比1%∶99%到99%∶1%;所述杀菌组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀菌组合物防治的植物病害选自:稻苗绵腐病、番茄根腐病、马铃薯晚疫病、烟草黑胫病、谷子白粉病、葡萄霜霉病、莴苣霜霉病、黄瓜霜霉病、黄瓜炭疽病;所述杀菌组合物适用的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
7.权利要求1所述的吡唑酰胺衍生物Ⅷ与抗植物病毒剂组合在防治农业和林业以及园艺植物病毒病害中的用途:
权利要求1所述的吡唑酰胺衍生物Ⅷ与商品抗病毒药剂中的任意一种或两种组合形成抗病毒组合物用于防治农业和林业以及园艺植物病毒病害,所述商品抗病毒药剂选自:苯并噻二唑、噻酰菌胺,简写为TDL、异噻菌胺,其英文通用名为:isotianil、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、DL-β-氨基丁酸、病毒唑、安托芬、宁南霉素、噻酰胺、甲噻诱胺或水杨酸、嘧肽霉素、二氯异烟酸、烯丙异噻唑、井冈羟胺、井冈霉素;权利要求1所述的吡唑酰胺衍生物Ⅷ在所述抗病毒组合物中的总的质量百分含量是1%-90%,权利要求1所述的吡唑酰胺衍生物Ⅷ与前述商品抗植物病毒剂的比例为质量百分比1%∶99%到99%∶1%;所述抗病毒组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述抗病毒组合物防治的病毒病害选自:水稻矮缩病、黄矮病、条纹叶枯病、番茄蕨叶病毒病、辣椒花叶病毒病、烟草脉坏死病毒病、玉米矮花叶病、花椰菜花叶病毒、柑橘病毒病、建兰花叶病毒、建兰环斑病毒;所述抗病毒组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
8.权利要求1所述的吡唑酰胺衍生物Ⅷ与杀螨剂组合在防治农业和林业以及园艺植物病毒病害中的用途:
权利要求1所述的吡唑酰胺衍生物Ⅷ与商品杀螨剂中的任意一种或两种组合形成杀螨组合物用于防治农业和林业以及园艺植物螨害,所述商品杀螨剂选自:三唑锡、三环锡、苯丁锡、三磷锡、毒虫畏、甲基毒虫畏、巴毒磷、敌敌畏、庚烯磷、速灭磷、久效磷、二溴磷、毒死蜱、嘧啶磷、氯甲亚胺硫磷、氧乐果、敌杀磷、乙硫磷、马拉硫磷、虫螨畏、伏杀硫磷、辛硫磷、甲基嘧啶硫磷、喹硫磷、治螟磷、三唑磷、蚜灭多、水胺硫磷、甲胺磷、胺丙畏、氯亚胺硫磷、亚胺硫磷、氟丙菊酯、联苯菊酯、氯氟氰菊酯、精高效氯氟氰菊酯、甲氰菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯、溴氟菊酯、联苯肼酯、苯硫威、涕灭威、丁酮威、杀线威、抗虫威、久效威、苯菌灵、氯灭杀威、克百威、丁硫克百威、速灭威、蜱虱威、伐虫脒、单甲脒、杀螨脒、双甲脒、杀虫脒、苯甲酸苄酯、溴螨酯、丁氟螨酯、灭螨醌、氟蚜螨、氟虫脲、浏阳霉素、虫螨霉素、苏云金素、杀螨素、浏阳霉素、阿维菌素、多拉菌素、埃普利诺菌素、伊维菌素、赛拉菌素、莫西菌素、除虫菊素、烟碱、苦参碱、印楝素、鱼藤酮、吡螨胺、哒螨酮、唑螨酯、四螨嗪、炔螨特、噻螨酮、螺螨酯、嘧螨酯、杀螨酯、克螨特、哒螨灵;权利要求1所述的吡唑酰胺衍生物Ⅷ在所述杀螨组合物中的总的质量百分含量是1%-90%,权利要求1所述的吡唑酰胺衍生物Ⅷ与所述商品杀螨剂的比例为质量百分比1%∶99%到99%∶1%;所述杀螨组合物加工的剂型选自:种子处理乳剂、水乳剂、微乳剂、悬乳剂、胶囊悬浮剂、水溶性粒剂、细粒剂、可溶性浓剂、毒谷、块状毒饵、粒状毒饵、片状毒饵、浓毒饵、缓释块、静电喷雾剂、水包油乳剂、烟雾罐、烟雾烛、烟雾筒、烟雾棒、烟雾片、烟雾丸、发气剂、油膏、热雾剂、冷雾剂、气雾剂、固/液混合装剂、液/液混合装剂、固/固混合装剂、药漆、微粒剂、追踪粉剂、油悬剂、油分散性粉剂、浓胶剂、泼浇剂、种衣剂、涂抹剂、成膜油剂、超低容量液剂、蒸汽释放剂;所述杀螨组合物防治的螨害选自:螨害选自叶螨科、细须螨科、呋线螨、瘿螨科、红叶螨属、瘿螨科的害螨,这些害螨是世界性农业害螨、林业害螨、园艺害螨和卫生害螨;所述杀螨组合物用于防治的植物选自:稻谷、小麦、大麦、燕麦、玉米、高粱、甘薯、马铃薯、木薯、大豆、荷兰豆、蚕豆、豌豆、绿豆、小豆、棉花、蚕桑、花生、油菜、芝麻、向日葵、甜菜、甘蔗、咖啡、可可、人参、贝母、橡胶、椰子、油棕、剑麻、烟草、番茄、辣椒、萝卜、黄瓜、白菜、芹菜、榨菜、甜菜、油菜、葱、大蒜、西瓜、甜瓜、哈密瓜、木瓜、苹果、柑桔和桃树、茶、山野菜、竹笋、啤酒花、胡椒、香蕉、番木瓜、兰花、盆景。
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