Synthesis and herbicidal application of turpentine derivative p-menthene type secondary amines as sustainable agrochemicals

2020 ◽  
Vol 44 (20) ◽  
pp. 8280-8288 ◽  
Author(s):  
Huanhuan Dong ◽  
Shichao Xu ◽  
Jing Wang ◽  
Hongmei Zhang ◽  
Yuxiang Chen ◽  
...  

Compound 3a showed excellent herbicidal activity against barnyard grass with IC50 = 7.0 mg L−1, and exhibited good selection for rice, wheat, and radish at 100 mg L−1.

2020 ◽  
Vol 76 (6) ◽  
pp. 2058-2067
Author(s):  
Lanxiang Xiang ◽  
Lei Zhang ◽  
Qinglai Wu ◽  
Zhihong Xu ◽  
Junkai Li ◽  
...  

2021 ◽  
Vol 9 ◽  
Author(s):  
Dingfeng Luo ◽  
Haodong Bai ◽  
Xiaomao Zhou ◽  
Lamei Wu ◽  
Chengjia Zhang ◽  
...  

To enhance quinclorac potency, twenty-five derivatives were synthesized containing 3-methyl-1H-pyrazol-5-yl by intermediate derivatization methods (IDMs). These compounds were confirmed by melting point (mp), 1HNMR, 13CNMR, and HRMS. The compound 1,3-dimethyl-1H-pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate (10a) was determined by X-ray diffraction. The activity of these compounds substituent on the phenyl was: electron-drawing group > neutral group > donor-drawing group, the results was like that of substituted benzyl group on pyrazole. The herbicidal activity assays showed that compounds 1-(2-fluorophenyl)-3-methyl-1H-pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate (8l, EC50 = 10.53 g/ha) and 10a (EC50 = 10.37 g/ha) had an excellent inhibition effect on barnyard grass in greenhouse experiment. Greenhouse safety experiment of rice exhibited almost no difference in plant height and fresh weight treated 10a at stage 1∼2-leaf of rice after 14 days but 8l had a detrimental effect. Two season field assays showed 10a herbicidal activity on barnyard grass at 150 g/ha as equal as 300 g/ha quinclorac in fields in 2019 and 2020. The study demonstrated that 10a could be further researched as a potential herbicide to control barnyard grass in fields.


RSC Advances ◽  
2021 ◽  
Vol 11 (44) ◽  
pp. 27207-27214
Author(s):  
Hongmei Zhang ◽  
Yuxiang Chen ◽  
Shichao Xu ◽  
Jing Wang ◽  
Huanhuan Dong ◽  
...  

In this study, a series of novel sec-p-menthane-7-amine derivatives were designed, synthesized, and evaluated to be used as efficient botanical herbicides owing to their post-emergence herbicidal activities against barnyard grass and rape.


Author(s):  
Gul’nara Z. Raskil’dina ◽  
Evgeniya A. Yakovenko ◽  
Luisa M. M. Mryasova ◽  
Simon S. Zlotskii

The herbicidal activity of esters and amides based on commercially available phenoxy chlorides and 2,4-dichlorophenoxyacetic acids was studied. Esters of 2,2-methyl-4-hydroxymethyl-1,3-dioxolane, 5-ethyl-5-hydroxymethyl-1,3-dioxane and 1,3-dioxolan-4-ylmethanol and 1,3-dioxane-5 -ol (glycerin formulas), as well as amides containing gem-dichlorocyclopropane and 1,3-dioxolane fragments were obtained. The acid chlorides, 1,3-dioxacycloalkanes and secondary amines were prepared according to standard basic methods. Esters and amides were synthesized from these starting compounds in a short time and with a quantitative yield (more than 90%). As a result of the synthesis of a mixture of 1,3-dioxolan-4-ylmethyl phenylacetate and 1,3-dioxan-5-yl phenylacetate, the content of the 5-ring cyclic derivative over the 6-chain structure was predominant, which is obviously associated with greater activity in the esterification reaction of primary alcohol than secondary. The screening results showed that the activity relative to wheat of the 1,3-dioxalane ester of 2,4-dichlorophenoxyacetic acid is superior to the Octagon-Extra standard. With respect to peas, derivatives of 2,4-dichlorophenoxyacetic acid and 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane are close to the standard for inhibition of shoot mass. The results of N-benzyl-N-[(2,2-dichlorocyclopropyl) methyl] -2-phenoxyacetamide and N-[(2,2-dichlorocyclopropyl) methyl]-N-(1,3-dioxolan-4-ylmethyl)-2-phenoxyacetamide with respect to peas and wheat also showed a marked herbicidal effect, close in value to the reference one. The test results of synthesized benzamides on wheat showed that, at a concentration of 100 mg/l, the compounds act approximately the same as the reference preparation at a dose of 50 mg/l. The obtained results prove the prospects of creating herbicidal preparations based on phenoxy- chlorides and 2,4-dichlorophenoxyacetic acids containing 1,3-dioxacycloalkane fragments. Therefore, these objects are very attractive for further study and synthesis of biologically active compounds containing the above pharmacophore groups.


2016 ◽  
Vol 5 (4) ◽  
Author(s):  
Leslie Aitken

Lee, Dennis.  Melvis and Elvis.  Illus. Jeremy Tankard. Toronto: Harper Collins, 2015. Print.In this new anthology of poetry for children, the inimitable Dennis Lee lets us explore our moods: silly or serious, playful or pugnacious, riotous, rebellious and just plain rude. In typical Lee fashion, he eschews sentimentality:            The dog got fat—            His belly exploded            And that was that.                                       (“Cabbagetown,” p. 22)but he is also capable of stealing the heart with simple, lovely metaphor:            Bobolink, bobolink,            Take me along.            I’ll be the silence            And you be the song.                                        (“Bobolink,” p. 21)He teases the tongue with creative wordplay (a Dennis Lee trademark):            I thought I saw a potamus,            Asleep upon a cotamus,            But when I reached the spotamus,            The potamus was notamus.                                        (“The Notapotamus,” p. 29)Ever true to his audience, he does not flinch from the reality of childhood emotion, be it longing:            If you could like me,            Like me now,            As deep as the dreams            In your heart allow.                                           (“The New Friend,” p. 30)or loathing:            Doodle, doodle, poppyseed strudel,            I’ve got a friend and he smells like a poodle.                        * * *            Push him down a wishing well—            Still can’t stop that awful smell.                                                (“Stinkarama,” p. 26) The book is cleverly structured, beginning and ending with poems about Melvis the monster and Elvis the elf, the final selection subtly acknowledging both the “inner monster” and the “inner elf” of the child.Jeremy Tankard’s illustrations are highly suited to the text.  He uses bold outline, vivid color, and complementary backgrounds to effect focus, clarity and mood.  Preschoolers and beginning readers should have no trouble relating poem and picture.This is a book that could be shared repeatedly with children at bedtime or in storyhour.  However, a parent, teacher, or librarian would want occasionally to interject, “Do we sometimes feel like that?  Would we actually say that or do that?” That being understood, it is a good selection for home, school and public libraries.Recommended: 3 out of 4 starsReviewer:  Leslie AitkenLeslie Aitken’s long career in librarianship involved selection of children’s literature for school, public, special, and university collections.  She is a former Curriculum Librarian at the University of Alberta.


Holzforschung ◽  
2011 ◽  
Vol 65 (2) ◽  
Author(s):  
Wen-Gui Duan ◽  
Xing-Ren Li ◽  
Qi-Jin Mo ◽  
Jian-Xin Huang ◽  
Bo Cen ◽  
...  

Abstract To search for novel therapeutic compounds with higher activity, a series of novel dehydroabietic acid derivatives bearing 1,3,4-oxadiazole moieties were designed and synthesized. Ten title compounds 5-dehydroabietyl-2-alkyl thio-1,3,4-oxadiazoles were synthesized by the reaction of 5-dehydroabietyl-2-mercapto-1,3,4-oxadiazole with alkyl halide or substituted benzyl halide in ethanolic KOH. All the title compounds were analyzed and characterized by means of IR, UV-vis, EI-MS, 1H-NMR, 13C-NMR, and elemental analysis. The preliminary herbicidal assay showed that almost all of the compounds exhibited an excellent growth inhibition to rape (Brassica campestris) and a certain inhibition to barnyard grass (Echinochloa crusgalli L.) at a concentration of 100 μg ml-1.


Sign in / Sign up

Export Citation Format

Share Document