scholarly journals Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

2020 ◽  
Vol 16 ◽  
pp. 233-247 ◽  
Author(s):  
Man-Man Wang ◽  
Hao Huang ◽  
Lei Shu ◽  
Jian-Min Liu ◽  
Jian-Qiu Zhang ◽  
...  

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (K i = 0.011 µM) and I23 (K i = 0.012 µM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (K i = 0.013 µM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

2019 ◽  
Author(s):  
Man-Man Wang ◽  
Hao Huang ◽  
Lei Shu ◽  
Jian-Min Liu ◽  
Jian-Qiu Zhang ◽  
...  

A series of aryloxyacetic acid derivatives were designed and synthesized as HPPD inhibitors. The preliminary bioassay results indicated that these derivatives displayed promising Arabidopsis thaliana HPPD (AtHPPD) inhibitory activity, such as compound I12 (K i = 0.011 µM) and compound I23 (K i = 0.012 µM), which were similar with commercial HPPD herbicide Mesotrione (K i = 0.013 µM). Furthermore, the newly synthesized compounds showed significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, compound II4 exhibited highly herbicidal activity for pre-emergence treatment, even better than those of Mesotrione. Besides, compound II4 was safe for weed control in maize fields at the rate of 150 g ai/ha. Therefore, compound II4 was identified as the most potent candidate for novel HPPD inhibitor herbicide. Compounds described herein might provide useful ideas in the design and modification of new HPPD inhibiting-based herbicides.


Weed Science ◽  
1993 ◽  
Vol 41 (3) ◽  
pp. 347-352 ◽  
Author(s):  
Glenn R. Wehtje ◽  
John W. Wilcut ◽  
John A. Mcguire

Mixtures of chlorimuron and 2,4-DB were additive with respect to crop injury and were either additive or slightly antagonistic with respect to weed control in greenhouse experiments. Absorption and translocation of14C following application of14C-chlorimuron and14C-2,4-DB were not affected by the presence of the other unlabeled herbicide, except in Florida beggarweed and peanut where 2,4-DB affected distribution of14C-chlorimuron in the treated leaf. In field studies, maximum efficacy was obtained with mixtures of chlorimuron plus 2,4-DB applied 7 or 9 wk after planting. Florida beggarweed control was greatest with chlorimuron or chlorimuron mixtures while the addition of 2,4-DB to chlorimuron improved morningglory and sicklepod control. At 9 and 11 wk after planting, addition of 2,4-DB to chlorimuron controlled Florida beggarweed better than chlorimuron alone. Peanut yields were increased by the addition of 2,4-DB at later applications.


Weed Science ◽  
1982 ◽  
Vol 30 (2) ◽  
pp. 169-174 ◽  
Author(s):  
Victor Raboy ◽  
Herbert J. Hopen

The persistence and effectiveness in pumpkin [Cucurbita moschata(Puch.) Poir.] weed control of several starch xanthide (SX) and commercial formulations of the ammonium (NH3) salt and methyl (CH3) ester of chloramben (3-amino-2,5-dichlorobenzoic acid) were studied in the laboratory and field. The soluble concentrate (SC) of chloramben NH3salt and the emulsifiable concentrate (EC) of chloramben CH3ester controlled weeds throughout the growing season on a silt loam soil. SC chloramben NH3salt was not effective, and EC chloramben CH3ester was inconsistent in weed control on sandy soil. Manipulation of the SX formulation produced products with slow, uniform release rates. The release rates (crosslinking reagent in parenthesis) rank as follows, from fastest to slowest: SX(Ca2+) CH3ester = SX(H2O2) acid > SX(H2O2) CH3ester > SX(Fe3+) acid > SX(Fe3+) CH3ester. In trials on silt loam and sand, SX formulations did not control weeds better than EC chloramben CH3ester.


1998 ◽  
Vol 12 (2) ◽  
pp. 268-274 ◽  
Author(s):  
Robert C. Scott ◽  
David R. Shaw ◽  
Randall L. Ratliff ◽  
Larry J. Newsom

Greenhouse and field experiments were conducted to evaluate early postemergence (POST) tank mixtures of SAN 582 with fluazifop-P, imazethapyr, or sethoxydim. In the greenhouse, SAN 582 synergistically improved barnyardgrass, broadleaf signalgrass, and johnsongrass control from imazethapyr and sethoxydim. Half-rates of imazethapyr and sethoxydim tank-mixed with SAN 582 controlled grass weeds as well as full rates of either herbicide applied alone. Grass weed control with imazethapyr increased up to 40% with the addition of SAN 582. In field experiments, SAN 582 increased grass control with imazethapyr to a lesser degree than observed in the greenhouse. In a multispecies study, grass weed control increased up to 15% when SAN 582 was tank-mixed with a reduced rate of imazethapyr, although the full rate of imazethapyr applied POST with or without SAN 582 controlled grass weeds 80% or less. The combination of SAN 582 with sethoxydim was synergistic for barnyardgrass and johnsongrass control in this experiment. When applied POST in soybean, SAN 582 plus fluazifop-P or sethoxydim controlled barnyardgrass throughout the season better than a single POST application of a graminicide.


Weed Science ◽  
1990 ◽  
Vol 38 (3) ◽  
pp. 267-272 ◽  
Author(s):  
Steven G. Russell ◽  
Thomas J. Monaco ◽  
Jerome B. Weber

Field trials were conducted in 1986 and 1987 to determine the effects of moisture on herbicidal activity of cinmethylin applied preemergence at 0.0, 0.3, 0.6, and 0.9 kg ai ha to both dry and moist sandy loam soil. Herbicide application was followed by varying amounts of irrigation. Weed species included velvetleaf, prickly sida, green foxtail, and barnyardgrass. When cinmethylin was applied to a moist soil or when 2.5 cm of irrigation was applied 5 days after cinmethylin application to a dry soil, overall weed control was reduced. Optimum weed control resulted from cinmethylin application to dry soil followed either by a 2.5-cm irrigation within 8 h or a 7.6-cm irrigation within 36 h.


1988 ◽  
Vol 2 (3) ◽  
pp. 262-264 ◽  
Author(s):  
Stanley F. Gorski ◽  
Stephen Reiners ◽  
Richard Hassell

Chloramben effectively controlled weeds in lettuce and endive grown on muck soils better than thiobencarb and chlorpropham. Chloramben at 1.1 kg ai/ha controlled two weeds economically important on muck soils, livid amaranth and oakleaf goosefoot. Chloramben applied preemergence at 1.1 kg/ha and higher caused early stunting of lettuce which the lettuce outgrew by harvest. Field-seeded endive was stunted severely at these same rates, severely reducing yield. Transplants improved tolerance of all crops. Effective use rates on muck soils were 25% to 50% of those typically used on mineral soils.


Weed Science ◽  
1982 ◽  
Vol 30 (5) ◽  
pp. 498-502 ◽  
Author(s):  
Jeffrey F. Derr ◽  
Thomas J. Monaco

In greenhouse studies, soil organic matter reduced the herbicidal activity of ethalfluralin (N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine). Fifty percent inhibition (I5.0) values for barnyardgrass [Echinochloa crus-galli(L.) Beauv.] stand, injury, and shoot fresh weight increased as the soil organic-matter level increased. No difference in ethalfluralin tolerance was found among 16 cucumber (Cucumis sativusL.) cultivars. When grouped according to market type, fresh market cultivars tended to be injured more than pickling cultivars by excess ethalfluralin. Both shoots and roots of cucumber absorbed the herbicide, but exposure of roots to ethalfluralin was more toxic than exposure of shoots. Field studies indicated that with certain edaphic and environmental conditions, cucumbers can be injured by preemergence applications of ethalfluralin. Injury was greatest in a low organic-matter soil following a heavy rain. Ethalfluralin at 1.3 kg/ha gave adequate weed control in 1 and 3% organic-matter soils, but not in a 9% organic-matter soil.


2019 ◽  
Vol 33 (2) ◽  
pp. 258-262
Author(s):  
Chad Brabham ◽  
Jason K. Norsworthy ◽  
Craig A. Sandoski ◽  
Vijay K. Varanasi ◽  
Lauren M. Schwartz-Lazaro

AbstractBenzobicyclon is a new pro-herbicide being evaluated in the Midsouth United States as a post-flood weed control option in rice. Applications of benzobicyclon to flooded rice are necessary for efficacious herbicide activity, but why this is so remains unknown. Two greenhouse experiments were conducted to explore how herbicide placement (foliage only, flood water only, foliage and flood water simultaneously) and adjuvants (nonionic surfactant, crop oil concentrate, and methylated seed oil [MSO]) affect herbicide activity. The first experiment focused on importance of herbicide placement. Little to no herbicidal activity (<18% visual control) was observed on two- to four-leaf barnyardgrass, Amazon sprangletop, and benzobicyclon-susceptible weedy rice with benzobicyclon treatments applied to weed foliage only. In contrast, applications made only to the flood water accounted for >82% of the weed control and biomass reduction achieved when benzobicyclon was applied to flood water and foliage simultaneously. The second experiment concentrated on adjuvant type and benzobicyclon efficacy when applied to foliage and flood water simultaneously. At 28 days after treatment, benzobicyclon alone at 371 g ai ha−1 provided 29% and 67% control of three- to five-leaf barnyardgrass and Amazon sprangletop, respectively. The inclusion of any adjuvant significantly increased control, with MSO providing near-complete control of barnyardgrass and Amazon sprangletop. Furthermore, we used the physiochemical properties of benzobicyclon and benzobicyclon hydrolysate to derive theories to explain the complex activity of benzobicyclon observed in our study and in field trials. Benzobicyclon applications should contain an oil-based adjuvant and must be applied to flooded rice fields for optimal activity.


1989 ◽  
Vol 16 (2) ◽  
pp. 87-91 ◽  
Author(s):  
T. C. Mueller ◽  
P. A. Banks

Abstract RE-40885 (5-(methylamino)-2-phenyl-4-3-(trifluoromethyl phenyl)-3(2H)-furanone), a newly developed herbicide with soil and foliar activity, was evaluated for weed control in peanuts (Arachis hypogea L.). RE-40885 applied to the soil or foliage provided excellent Florida beggarweed (Desmodium tortuosum (Sw.) DC.) and prickly sida (Sida spinosa L.) control at rates of 0.56 to 1.12 kg ai/ha. Sequential applications of RE-40885 were needed to achieve &gt; 90% sicklepod (Cassia obtusifolia L.) control. Texas panicum (Panicum texanum Buckl.) was not adequately controlled by any of the RE-40885 treatments evaluated. Peanuts were not injured by RE-40885 at any of the evaluated rates or application times. The combination of RE-40885 and 2,4-DB applied early postemergence improved sicklepod control 8 weeks after planting when compared to either RE-40885 or 2,4-DB applied alone. The combination of R E-40885 and alachlor applied at peanut emergence improved morningglory (Ipomoea spp.) control 8 weeks after planting and increased peanut yield when compared to either applied alone. All treatments containing RE-40885 resulted in peanut yields that were significantly better than nontreated weedy control plots.


Weed Science ◽  
1973 ◽  
Vol 21 (3) ◽  
pp. 258-260
Author(s):  
D. C. Milbocker

Fall-applied 2-chloro-4,6-bis(ethylamino)-s-triazine (simazine) and α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (trifluralin) satisfactorily controlled annual and biennial weeds in tall bearded iris (Iris germanica L.). Increased application rates improved control of semitolerant weeds. Trifluralin controlled grass weeds better than simazine. Simazine caused leaf tip and root necrosis, and trifluralin prevented root growth of iris plants when incorporated in the root zone at high rates of application.


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