Activity of the botanical aphicides 1,5‐diphenyl‐1‐pentanone and 1,5‐diphenyl‐2‐penten‐1‐one on two species of Aphididnae

1,5‐Diphenyl‐1‐pentanone (A) and 1,5‐diphenyl‐2‐penten‐1‐one (B) are natural products extracted for the first time from Stellera chamaejasme. Laboratory bioassay showed that the two products have strong contact activity and very good anti‐feedant activity against Aphis gossypii and Schizaphis graminum. Both products showed dose‐dependent relationships for both forms of activity against the two aphids, the contact activity of B being about twice that of A. Both products were inferior to methomyl in contact activity but superior in anti‐feedant activity against the two aphids. This is the first report of aphicidal activity in these two compounds, which may represent a new class of aphicide. © 2001 Society of Chemical Industry     

New 2-phenyl-4,5,6,7-tetrahydro-2H-indazole derivatives as paddy field herbicides

A series of 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole derivatives containing various substituted isoxazolinylmethoxy groups at the 5-position of the benzene ring were synthesized and their herbicidal activities assessed under greenhouse and flooded paddy conditions. Among them, compounds having a phenyl or cyano substituent at the 3-position of the 5-methyl-isoxazolin-5-yl structure demonstrated good rice selectivity and potent herbicidal activity against annual weeds at 16-63 g AI ha(-1) under greenhouse conditions. Field trials indicated that these two compounds controlled a wide range of annual weeds rapidly with a good tolerance on transplanted rice seedlings by pre-emergence application. They showed a low mammalian and environmental toxicity in various toxicological tests.     

Synthesis and herbicidal activity of new oxazinone herbicides with a long-lasting herbicidal activity against Echinochloa oryzicola

Chemical modification of the herbicide 1-[2-(benzothiazol-2-yl)isopropyl]-4-methyl-3-phenyl-5H-pyrrolin-2-one (MI-2826) has revealed a new oxazinone herbicide, 3-[2-(7-chlorobenzothiazol-2-yl)isopropyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (MI-3069), for use in paddy fields. In comparing the phyototoxicity of the two herbicides to transplanted rice, the latter was superior to the former and kept the same predominant characteristic to control Echinochloa oryzicola Vasin for a long period of time owing to its long-lasting residual effect.     

Synthesis and antifungal activity of 2‐azetidinonyl‐5‐(2‐benzoylphenoxy)methyl‐1,3,4‐oxadiazoles against seed‐borne pathogens of Eleusine coracana (L.) Gaertn

BACKGROUND: Finger millet is a major food crop as well as feed and fodder for livestock, especially in regions of southern India. A sturdy crop to fluctuating environmental conditions, it can be cultivated in all seasons of the year. Leaf, neck and finger blast caused by Pyricularia grisea Sacc. and Bipolaris setariae (Saw.) Shoem, as well as leaf spot disease, Bipolaris nodulosa (Berk & M.A.Curtis) Shoem, are major production constraints in southern India. Apart from environmental conditions, the use of harvested seeds by farmers is a major reason for disease prevalence. Benzophenone analogues have been investigated for controlling phytopathogenic fungi. In addition, the most important applications of azetidin‐2‐ones are as antibiotics. Based on this information, the present study was conducted to explore the antifungal activity of integrated 2‐azetidinonyl and 1,3,4‐oxadiazoles moieties into a benzophenone framework. RESULTS: A simple high‐yielding method for the integration of heterocyclic rings, namely 2‐azetidinonyl, at the benzophenone nucleus has been achieved, starting from substituted 2‐hydroxybenzophenones under mild conditions on a wet solid surface using microwave irradiation. In the present study, an array of newly synthesised compounds, 2‐azetidinonyl‐5‐(2‐benzoylphenoxy)methyl‐1,3,4‐oxadiazoles, were screened for their antifungal property against blast and leaf spot causing fungi associated with the seeds of finger millet, cv. Indof‐9. CONCLUSION: Two of the newly synthesised compounds showed promising effects in depleting the incidence of seed‐borne pathogenic fungi of finger millet. The suppression of Pyricularia grisea and Bipolaris setariae resulted in enhanced seed germination and seedling growth. Copyright © 2009 Society of Chemical Industry     

Design, synthesis, insecticidal activity and structure-activity relationship of 3,3-dichloro-2-propenyloxy-containing phthalic acid diamide structures

BACKGROUND: Phthalic acid diamide derivatives are among the most important classes of synthetic insecticides. In this study, a 3,3‐dichloro‐2‐propenyloxy group, the essential active group of pyridalyl derivatives, was incorporated into phthalic acid diamide derivatives with the aim of combining the active groups to generate more potent insecticides. RESULTS: Thirty‐one new phthalic acid diamides were obtained, and these were characterised by ¹H and ¹³C NMR. The structure of N²‐[1,1‐dimethyl‐2‐(methoxy)ethyl]‐3‐iodo‐N¹‐[4‐(3,3‐dichloro‐2‐propenyloxy)‐3‐(trifluoromethyl)phenyl]‐1,2‐benzenedicarboxamide was determined by X‐ray diffraction crystallography. The insecticidal activities of the compounds against Plutella xylostella were evaluated. The title compounds exhibited excellent larvicidal activities against P. xylostella. Structure‐activity relationships revealed that varying the combination of aliphatic amide and aromatic amide moieties, or the nature and position of substituent Y on the aniline ring, could aid the design of structures with superior performance. CONCLUSION: A series of novel phthalic acid diamides containing a 3,3‐dichloro‐2‐propenyloxy group at the 4‐position of the aniline ring were designed and synthesised. Structure‐activity relationships with the parent structure provided information that could direct further investigation on structure modification. Copyright © 2012 Society of Chemical Industry     

Isoflucypram,the first representative of a new succinate dehydrogenase inhibitor fungicide subclass: Its chemical discovery and unusual binding mode

Succinate dehydrogenase inhibitors (SDHIs) have played a crucial role in disease control to protect cereals as well as fruit and vegetables for more than a decade. Isoflucypram, the first representative of a newly installed subclass of SDHIs inside the Fungicide Resistance Action Committee (FRAC) family of complex II inhibitors, offers unparalleled long‐lasting efficacy against major foliar diseases in cereals. Herein we report the chemical optimization from early discovery towards isoflucypram and the first hypothesis of its altered binding mode in the ubiquinone binding site of succinate dehydrogenase. © 2020 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.     

Identification of an ISR‐related metabolite produced by rhizobacterium Klebsiella oxytoca C1036 active against soft‐rot disease pathogen in tobacco

BACKGROUND: Klebsiella oxytoca C1036 (C1036) causes induced systemic resistance (ISR) activity against the soft‐rot pathogen Pectobacterium carotovorum subsp. carotovorum SCC1 (SCC1). However, microbial metabolites from C1036 involved in ISR activity remain unknown. The present study was performed to identify an ISR‐related metabolite produced by C1036. RESULTS: The supernatants of C1036 cultures grown on Luria‐Bertani medium were subjected to solvent extraction, repeated column chromatography and preparative liquid chromatography for isolation of an ISR‐related metabolite. High‐resolution mass spectrometer analysis of the isolated metabolite indicated a C₉H₁₅O₃N compound with a mass of 185.11. Low‐resolution mass spectrometer analysis of the metabolite showed a molecular ion peak at 185 and its fragment ions at 84 and 56. Nuclear magnetic resonance spectrometer analyses characterised all protons and carbons of the isolated metabolite. Based on the data, the isolated metabolite was determined to be butyl 2‐pyrrolidone‐5‐carboxylate (BPC). BPC at 12 mM significantly suppressed the disease symptoms in ISR bioassays against SCC1. CONCLUSION: This is the first report identifying BPC as an ISR‐related metabolite produced by C1036. C1036 may play a role in promoting plant growth because it produces ISR‐related metabolites against the plant pathogen SCC1. Copyright © 2009 Society of Chemical Industry     

Effect of application timing and method on efficacy and phytotoxicity of 1,3-D, chloropicrin and metam-sodium combinations in squash plasticulture

BACKGROUND: Metam-sodium, 1,3-dichloropropene (1,3-D) and chloropicrin are widely used soil fumigants. Combined application of metam-sodium and 1,3-D + chloropicrin is intended to improve efficacy and broaden spectrum of control, but little is known about the effect on crop safety. This study aimed to evaluate the effects of application timing of fumigant combinations on soilborne pest and disease control (nematodes, soil fungi and weeds) and growth of squash. Two separate tests with chisel-injected and drip-applied fumigant combinations and plant-back times ranging from 1 to 4 weeks were conducted in Tifton, GA, USA, in spring and fall 2002. RESULTS: Fumigant combinations using 1,3-D, chloropicrin and metam-sodium were as effective as methyl bromide in controlling Meloidogyne incognita (Kofoid & White) Chitwood, Pythium irregulare Buis., Rhizoctonia solani Kühn and Cyperus esculentus L. Chisel-applied combinations were more effective in terms of root-knot nematode control than drip-applied combinations. Root-knot nematode reduced squash yields by up to 60%. Phytotoxicity problems and lower yields were observed during spring, especially following 1,3-D + chloropicrin and when plant-back periods were shorter. CONCLUSION: The main problem with fumigant alternatives to methyl bromide may not be reduced efficacy but, in particular for 1,3-D products, loss of flexibility in terms of longer plant-back periods.