CN111436428A - Application of naphthaline benzylamine antifungal drugs in prevention and treatment of agricultural diseases - Google Patents
Application of naphthaline benzylamine antifungal drugs in prevention and treatment of agricultural diseases Download PDFInfo
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- 201000010099 disease Diseases 0.000 title claims abstract description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 23
- 239000003814 drug Substances 0.000 title claims abstract description 23
- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 22
- 229940079593 drug Drugs 0.000 title claims abstract description 22
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract description 20
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 title claims 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims 4
- 230000002265 prevention Effects 0.000 title abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 10
- 241000123650 Botrytis cinerea Species 0.000 claims abstract description 8
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- 229920000742 Cotton Polymers 0.000 claims abstract description 7
- 241000813090 Rhizoctonia solani Species 0.000 claims abstract description 6
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 7
- 229960000699 terbinafine hydrochloride Drugs 0.000 claims description 7
- SUMAWDZJEIQACJ-UHFFFAOYSA-N 2-methylpyridine-4-carbaldehyde Chemical compound CC1=CC(C=O)=CC=N1 SUMAWDZJEIQACJ-UHFFFAOYSA-N 0.000 claims description 5
- OLUNPKFOFGZHRT-YGCVIUNWSA-N Naftifine hydrochloride Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CN(C)C\C=C\C1=CC=CC=C1 OLUNPKFOFGZHRT-YGCVIUNWSA-N 0.000 claims description 5
- 229960003273 butenafine hydrochloride Drugs 0.000 claims description 5
- 229960003979 naftifine hydrochloride Drugs 0.000 claims description 5
- 239000003429 antifungal agent Substances 0.000 claims 5
- RBHDHUYOZLKADU-UHFFFAOYSA-N n-benzylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NCC1=CC=CC=C1 RBHDHUYOZLKADU-UHFFFAOYSA-N 0.000 claims 2
- OONMCMYNRVWSKN-UHFFFAOYSA-N (2-naphthalen-1-ylphenyl)methanamine Chemical compound NCC1=CC=CC=C1C1=CC=CC2=CC=CC=C12 OONMCMYNRVWSKN-UHFFFAOYSA-N 0.000 claims 1
- 241001330975 Magnaporthe oryzae Species 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 14
- 206010039509 Scab Diseases 0.000 abstract description 7
- 241000209140 Triticum Species 0.000 abstract description 7
- 235000021307 Triticum Nutrition 0.000 abstract description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 6
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 6
- 235000009566 rice Nutrition 0.000 abstract description 6
- 239000005730 Azoxystrobin Substances 0.000 abstract description 5
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 abstract description 5
- 239000000575 pesticide Substances 0.000 abstract description 4
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- 241000233866 Fungi Species 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 7
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 6
- 241000223218 Fusarium Species 0.000 description 6
- 241000209094 Oryza Species 0.000 description 5
- 230000003032 phytopathogenic effect Effects 0.000 description 5
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- 241000196324 Embryophyta Species 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 244000000003 plant pathogen Species 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
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- 241000005783 Monographella albescens Species 0.000 description 1
- 208000010195 Onychomycosis Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
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- 210000004027 cell Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000008686 ergosterol biosynthesis Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000021393 food security Nutrition 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
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- 206010037844 rash Diseases 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
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- 201000005882 tinea unguium Diseases 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了萘苄胺类抗真菌药物作为农药杀菌剂在农作物病害防治上的新用途，所述的萘苄胺类抗真菌药物为盐酸萘替芬、盐酸特比萘芬、盐酸布替萘芬，可防治由立枯丝核菌、油菜菌核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌引起的农作物病害，尤其是盐酸特比萘芬和盐酸布替萘芬对油菜菌核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌均表现出优异的抗菌作用，显著高于商品化杀菌剂嘧菌酯，可以在农作物病害防治上实现新用途。The invention discloses a new use of naphthylbenzylamine antifungal drugs as pesticides and fungicides in the prevention and control of crop diseases. Fen, can prevent and treat crop diseases caused by Rhizoctonia solani, Sclerotinia sclerotiorum, Tomato Botrytis cinerea, Fusarium oxysporum, M. Fenfen exhibited excellent antibacterial effects against Sclerotinia sclerotiorum, tomato gray mold, wheat scab, rice blast, and cotton wilt, which was significantly higher than the commercial fungicide azoxystrobin, which can be used in crop disease control. new use.
Description
技术领域technical field
本发明涉及农用杀菌剂领域，更具体地，涉及萘苄胺类抗真菌药物作为农用杀菌剂在防治农作物病害上的用途。The invention relates to the field of agricultural fungicides, more particularly, to the use of naphthylbenzylamine antifungal drugs as agricultural fungicides in preventing and treating crop diseases.
背景技术Background technique
植物病害严重威胁农业健康发展和粮食安全问题，因植物病害每年造成的粮食损失已超过产量的11％。比如我国稻田受到纹枯病的影响，每年造成600万吨谷物的损失，小麦受赤霉病的影响，每年造成10％～30％的减产。植物病害的严重发生、病原菌抗性的发展以及化学杀菌剂的滥用等，加剧植物病原菌对杀菌剂的抗性，严重威胁环境安全和人类健康。因此研究与开发能有效控制植物病原菌的高效、低毒、低残留的新型农药，已成为目前农药创制的首要目标。Plant diseases seriously threaten the healthy development of agriculture and food security, and the annual food loss caused by plant diseases has exceeded 11% of the output. For example, my country's paddy fields are affected by sheath blight, causing a loss of 6 million tons of grain every year, and wheat is affected by scab, causing an annual yield reduction of 10% to 30%. The serious occurrence of plant diseases, the development of pathogen resistance and the abuse of chemical fungicides have intensified the resistance of plant pathogens to fungicides, seriously threatening environmental safety and human health. Therefore, research and development of new pesticides with high efficiency, low toxicity and low residues that can effectively control plant pathogens has become the primary goal of pesticide creation.
盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬(结构式如式1所示)是一种萘苄胺类抗真菌药物，其作用机制为选择性地抑制真菌角鲨烯环氧化酶，干扰真菌细胞壁的麦角固醇的生物合成，影响真菌的脂质代谢，使真菌细胞损伤或死亡而起到杀菌和抑菌作用。具有抗菌谱广，毒性较低等特点，对皮肤真菌有杀菌作用，对白色念珠菌则起抑菌作用。常用于治疗皮肤及其附件(毛发、指甲、趾甲)等由发癣菌属、小孢子菌属及表皮癣菌属所致皮肤真菌感染，浅表念珠菌病、甲癣、花斑糖疹。但到目前为止，还未见萘苄胺类抗真菌医药在防治植物病原真菌方面的研究报道。基于此，本发明以3个萘苄胺类抗真菌药物为研究对象，评价其对植物病原真菌的抗菌活性，发现盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬对油菜菌核病菌，立枯丝核菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌均具有优异的抑制作用，显著优于商品化杀菌剂嘧菌酯，特别是盐酸特比萘芬和盐酸布替萘芬对油菜菌核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌5种真菌的抑菌活性最强。因此，萘苄胺类抗真菌药物作为防治重要农作物病害的杀菌剂有良好的开发前景。Naftifine hydrochloride, terbinafine hydrochloride and butenafine hydrochloride (structural formula shown in formula 1) are a kind of naphthylbenzylamine antifungal drugs, and their mechanism of action is to selectively inhibit fungal squalene epoxidation Enzymes interfere with the biosynthesis of ergosterol in the fungal cell wall, affect the lipid metabolism of fungi, damage or die of fungal cells and play a bactericidal and bacteriostatic effect. It has the characteristics of broad antibacterial spectrum and low toxicity. It has bactericidal effect on skin fungi and antibacterial effect on Candida albicans. It is commonly used to treat skin and its accessories (hair, nails, toenails) and other dermatophyte infections caused by Trichophyton, Microsporum and Epidermophyton, superficial candidiasis, onychomycosis, and piebald rash. But so far, there are no research reports on naphthylbenzylamine antifungal drugs in the control of plant pathogenic fungi. Based on this, the present invention takes 3 naphthobenzylamine antifungal drugs as research objects, and evaluates their antibacterial activities against phytopathogenic fungi. Bacteria, Rhizoctonia solani, tomato botrytis cinerea, wheat scab, rice blast, cotton fusarium wilt all have excellent inhibitory effect, significantly better than commercial fungicides azoxystrobin, especially terbinafine hydrochloride And butenafine hydrochloride had the strongest antibacterial activity against five fungi, Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium oryzae, M. oryzae and Fusarium wilt. Therefore, naphthylbenzylamine antifungal drugs have good development prospects as fungicides for controlling important crop diseases.
式1.3种萘苄胺类抗真菌医药 Formula 1.3 kinds of naphthylbenzylamine antifungal medicines
发明内容SUMMARY OF THE INVENTION
本发明的目的是将用于医药方面的萘苄胺类3个杀真菌药剂用于农作物病害的防治，以扩大各药剂的使用范围，拓展其新用途，实现“老药新用”，以期筛选到一些高效、低毒的农药杀菌剂。The purpose of the present invention is to use the three fungicidal agents of naphthobenzylamines used in medicine for the prevention and treatment of crop diseases, to expand the scope of use of each agent, to expand its new use, to realize "new use of old drugs", with a view to screening to some efficient and low-toxic pesticides and fungicides.
萘苄胺类抗真菌药物作为杀菌剂在农作物病害防治上的新用途，所述的萘苄胺类抗真菌医药为盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬，可防治由油菜菌核病菌、立枯丝核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌引起的农作物真菌病害。The new use of naphthylbenzylamine antifungal drugs as fungicides in the prevention and control of crop diseases, the naphthylbenzylamine antifungal drugs are naftifine hydrochloride, terbinafine hydrochloride and butenafine hydrochloride, which can prevent and treat diseases caused by Crop fungal diseases caused by Sclerotinia sclerotiorum, Rhizoctonia solani, tomato Botrytis cinerea, wheat scab, rice blast, cotton fusarium wilt.
与现有技术相比，本发明的效果是：萘苄胺类抗真菌药物(盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬)对多种农作物真菌病害的活性显著高于农用商品化杀菌剂嘧菌酯，可以在农业农作物病害防治上实现新用途。Compared with the prior art, the effect of the present invention is: the activity of naphthylbenzylamine antifungal drugs (naftifine hydrochloride, terbinafine hydrochloride and butinafine hydrochloride) to various crop fungal diseases is significantly higher than that of agricultural use. The commercial fungicide azoxystrobin can achieve new uses in the prevention and control of agricultural crop diseases.
具体实施方式Detailed ways
萘苄胺类抗真菌药物作为杀菌剂在农作物病害防治上的新用途，所述的萘苄胺类抗真菌药物为盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬，可防治由油菜菌核病菌、立枯丝核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌引起的农作物真菌病害。The new use of naphthylbenzylamine antifungal drugs as fungicides in the prevention and control of crop diseases. Crop fungal diseases caused by Sclerotinia sclerotiorum, Rhizoctonia solani, tomato Botrytis cinerea, wheat scab, rice blast, cotton fusarium wilt.
以下是本发明的具体实施例，对本发明的技术方案做进一步描述，但本发明的内容不仅仅局限于实施例所述的范围，凡是不背离本发明构思的改变或等同替代均包括在本发明的保护范围之内。The following are specific embodiments of the present invention to further describe the technical solutions of the present invention, but the content of the present invention is not limited to the scope described in the embodiments, and any changes or equivalent substitutions that do not deviate from the concept of the present invention are included in the present invention. within the scope of protection.
实施例：室内抑菌活性测定及结果Example: Determination of indoor antibacterial activity and results
采用菌丝生长速率法：按照一定的浓度梯度，将测试化合物加入经灭菌并冷却至50℃左右的培养基中，混匀，将药剂稀释成系列浓度制备成含药培养基，每培养皿接种一菌碟(直径d＝5mm)，每个浓度设置3个重复；并以嘧菌酯为对照药剂，测定化合物对6种植物病原真菌的抑制活性。在25℃培养至对照菌落长满培养皿2/3以上时以十字交叉法测定各浓度处理的菌落直径(mm)，取其平均值代表，计算药剂对菌丝体的生长抑制率，差异性统计分析采用统计软件SAS8.1(StatisticalAnalysisSystem8.1)进行。测定3种萘苄胺类抗真菌医药对6种植物病原真菌的抑制效果，结果见表1和表2。Using the mycelial growth rate method: according to a certain concentration gradient, add the test compound to the sterilized medium cooled to about 50 °C, mix well, and dilute the drug to a series of concentrations to prepare a drug-containing medium. A bacterial plate (diameter d=5mm) was inoculated, and three replicates were set for each concentration; and azoxystrobin was used as a control agent to determine the inhibitory activity of the compounds against 6 phytopathogenic fungi. When cultured at 25°C until the control colony covered more than 2/3 of the petri dish, the diameter (mm) of the colonies treated with each concentration was measured by the cross method, and the average value was taken as the representative, and the growth inhibition rate of the drug on the mycelium was calculated. Statistical analysis was performed using statistical software SAS8.1 (Statistical Analysis System 8.1). The inhibitory effects of 3 kinds of naphthylbenzylamine antifungal medicines on 6 kinds of phytopathogenic fungi were determined, and the results are shown in Table 1 and Table 2.
表1.3种萘苄胺类抗真菌药物对植物病原真菌的抑制活性Table 1. Inhibitory activity of three naphthobenzylamine antifungal drugs against phytopathogenic fungi
注：-:没有测定Note: -: Not measured
表2.3种萘苄胺类抗真菌医药对植物病原真菌的抑制活性Table 2. Inhibitory activity of three naphthylbenzylamine antifungal drugs against phytopathogenic fungi
由表1和表2生测结果可知，本发明涉及的3种萘苄胺类抗真菌药物(盐酸萘替芬、盐酸特比萘芬和盐酸布替萘芬)对油菜菌核病菌，立枯丝核菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌均表现出优异的抑制作用，显著高于同浓度下的商品化杀菌剂嘧菌酯。特别是盐酸特比萘芬和盐酸布替萘芬对油菜菌核病菌、番茄灰霉病菌、小麦赤霉病菌、稻瘟病菌、棉花枯萎病菌5种真菌的抑菌活性最强，其EC50值分别为0.80、0.11、0.17、0.26、0.30μg/mL和0.22、 0.07、0.08、0.29、0.24μg/mL。综上所述，本发明所述的萘苄胺类抗真菌药物对农业病菌表现出显著的抑制活性，可以在农作物病害防治上实现新用途。From table 1 and table 2 bioassay results, 3 kinds of naphthylbenzylamine antifungal drugs (naftifine hydrochloride, terbinafine hydrochloride and butenafine hydrochloride) involved in the present invention are to Sclerotinia sclerotiorum, Rhizoctonia solani. Rhizoctonia, botrytis cinerea, wheat scab, rice blast and cotton fusarium wilt all showed excellent inhibitory effects, which were significantly higher than the commercial fungicides azoxystrobin at the same concentration. In particular, terbinafine hydrochloride and butinafine hydrochloride have the strongest antibacterial activity against five fungi, Sclerotinia sclerotiorum, tomato botrytis cinerea, wheat scab, rice blast and cotton wilt, and their EC 50 values were 0.80, 0.11, 0.17, 0.26, 0.30 μg/mL and 0.22, 0.07, 0.08, 0.29, 0.24 μg/mL, respectively. To sum up, the naphthylbenzylamine antifungal drugs of the present invention show significant inhibitory activity against agricultural pathogens, and can achieve new uses in the prevention and control of crop diseases.
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