Paper · 2021 · Journal of Agricultural and Food Chemistry

Rational Optimization of 1,2,3-Triazole-Tailored Carbazoles As Prospective Antibacterial Alternatives with Significant In Vivo Control Efficiency and Unique Mode of Action

Xing Huang; Hong-Wu Liu; Zhou-Qing Long; et al.

10
claims
15
verbatim quotes
75
citations
2
research areas
—
Not open access

Abstract

Plant bacterial diseases can potentially damage agricultural products around the world, and few effective bactericides can manage these infections. Herein, to sequentially explore highly effective antibacterial alternatives, 1,2,3-triazole-tailored carbazoles were rationally fabricated. These compounds could suppress the growth of three main intractable pathogens including Xanthomonas oryzae pv oryzae (Xoo), X. axonopodis pv citri (Xac), and Pseudomonas syringae pv actinidiae (Psa) with lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 μg/mL (3r), respectively. Pot experiments revealed that compound 3p could control the rice bacterial blight with protective and curative efficiencies of 53.23% and 50.78% at 200 μg/mL, respectively. Interestingly, the addition of 0.1% auxiliaries such as organic silicon and orange oil could significantly enhance the surface wettability of compound 3p toward rice leaves, resulting in improved control effectiveness of 65.50% and 61.38%, respectively. Meanwhile, compound 3r could clearly reduce the white pyogenic exudates triggered by Psa infection and afforded excellent control efficiencies of 79.42% (protective activity) and 78.74% (curative activity) at 200 μg/mL, which were quite better than those of commercial pesticide thiodiazole copper. Additionally, a plausible apoptosis mechanism for the antibacterial behavior of target compounds was proposed by flow cytometry, reactive oxygen species detection, and defensive enzyme (e.g., catalase and superoxide dismutase) activity assays. The current work can promote the development of 1,2,3-triazole-tailored carbazoles as prospective antibacterial alternatives bearing an intriguing mode of action.

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Claims 10

Observationobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3p suppressed Xoo growth with EC50 3.36 μg/mL.

Treatment
3pe1
Interactor
Xanthomonas oryzae pv oryzaeXanthomonas oryzaee0pathogen
Outcome
EC50 valuese1
Value
3.36e1

Not reportedTaxon

Verbatim

e0

“Xanthomonas oryzae pv oryzae (Xoo)”

✓ located verbatim in the source · abstract, characters 376–410 · show in text ↑
e1

“lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 μg/mL (3r), respectively”

✓ located verbatim in the source · abstract, characters 492–568 · show in text ↑
Observationobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3p suppressed Xac growth with EC50 2.87 μg/mL.

Treatment
3pe1
Interactor
X. axonopodis pv citriXanthomonas axonopodise0pathogen
Outcome
EC50 valuese1
Value
2.87e1

Not reportedTaxon

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Xanthomonas axonopodis
Xanthomonas axonopodis · InteractorPublic domain · Wikimedia Commons ↗

Verbatim

e0

“X. axonopodis pv citri (Xac)”

✓ located verbatim in the source · abstract, characters 412–440 · show in text ↑
e1

“lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 μg/mL (3r), respectively”

✓ located verbatim in the source · abstract, characters 492–568 · show in text ↑
Observationobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3r suppressed Psa growth with EC50 4.57 μg/mL.

Treatment
3re1
Interactor
Pseudomonas syringae pv actinidiaePseudomonas syringaee0pathogen
Outcome
EC50 valuese1
Value
4.57 μg/mLe1

Not reportedTaxon

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Pseudomonas syringae
Pseudomonas syringae · InteractorHoward F. Schwartz · CC BY 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“Pseudomonas syringae pv actinidiae (Psa)”

✓ located verbatim in the source · abstract, characters 446–486 · show in text ↑
e1

“lower EC50 values of 3.36 (3p), 2.87 (3p), and 4.57 μg/mL (3r), respectively”

✓ located verbatim in the source · abstract, characters 492–568 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3p had 53.23% protective control efficiency against rice bacterial blight.

Treatment
compound 3pe0
Outcome
protectivee0
Direction
controle0
Value
53.23%e0

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Oryza sativa
Oryza sativa · Taxon · picture from its Wikimedia Commons categoryDesmanthus4food · CC BY-SA 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“compound 3p could control the rice bacterial blight with protective and curative efficiencies of 53.23% and 50.78% at 200 μg/mL, respectively”

✓ located verbatim in the source · abstract, characters 600–741 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3p had 50.78% curative control efficiency against rice bacterial blight.

Treatment
compound 3pe0
Outcome
curative efficienciese0
Direction
controle0
Value
50.78%e0

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Oryza sativa
Oryza sativa · Taxon · picture from its Wikimedia Commons categoryDesmanthus4food · CC BY-SA 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“compound 3p could control the rice bacterial blight with protective and curative efficiencies of 53.23% and 50.78% at 200 μg/mL, respectively”

✓ located verbatim in the source · abstract, characters 600–741 · show in text ↑
Intervention effectobservedoriginal resultpositivesignificant (as stated)measured

Claim · model-written summary

Organic silicon improved wettability of 3p on rice leaves and control effectiveness to 65.50%.

Organ / stage
leavese0
Treatment
organic silicone0
Outcome
surface wettability of compound 3p toward rice leavese0
Direction
enhancee0
Value
65.50%e0

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Oryza sativa
Oryza sativa · Taxon · picture from its Wikimedia Commons categoryDesmanthus4food · CC BY-SA 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“the addition of 0.1% auxiliaries such as organic silicon and orange oil could significantly enhance the surface wettability of compound 3p toward rice leaves, resulting in improved control effectiveness of 65.50% and 61.38%, respectively”

✓ located verbatim in the source · abstract, characters 758–995 · show in text ↑
Intervention effectobservedoriginal resultpositivesignificant (as stated)measured

Claim · model-written summary

Orange oil improved wettability of 3p on rice leaves and control effectiveness to 61.38%.

Organ / stage
leavese0
Treatment
orange oile0
Outcome
surface wettability of compound 3p toward rice leavese0
Direction
enhancee0
Value
61.38%e0

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Oryza sativa
Oryza sativa · Taxon · picture from its Wikimedia Commons categoryDesmanthus4food · CC BY-SA 3.0 us · Wikimedia Commons ↗

Verbatim

e0

“the addition of 0.1% auxiliaries such as organic silicon and orange oil could significantly enhance the surface wettability of compound 3p toward rice leaves, resulting in improved control effectiveness of 65.50% and 61.38%, respectively”

✓ located verbatim in the source · abstract, characters 758–995 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3r reduced white pyogenic exudates induced by Psa.

Treatment
compound 3re0
Interactor
Psae0pathogen
Outcome
white pyogenic exudates triggered by Psa infectione0
Direction
reducee0

Not reportedTaxonComparator

Verbatim

e0

“compound 3r could clearly reduce the white pyogenic exudates triggered by Psa infection”

✓ located verbatim in the source · abstract, characters 1008–1095 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3r had 79.42% protective control efficiency against Psa.

Treatment
3re2
Interactor
Psae1pathogen
Outcome
protective activitye0
Direction
bettere0
Value
79.42%e0
Comparator
commercial pesticide thiodiazole coppere0

Not reportedTaxon

Verbatim

e0

“afforded excellent control efficiencies of 79.42% (protective activity) and 78.74% (curative activity) at 200 μg/mL, which were quite better than those of commercial pesticide thiodiazole copper”

✓ located verbatim in the source · abstract, characters 1100–1294 · show in text ↑
e1

“Psa infection”

✓ located verbatim in the source · abstract, characters 1082–1095 · show in text ↑
e2

“compound 3r could clearly reduce the white pyogenic exudates”

✓ located verbatim in the source · abstract, characters 1008–1068 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Compound 3r had 78.74% curative control efficiency against Psa.

Treatment
compound 3re0
Interactor
Psae0pathogen
Outcome
curative activitye0
Direction
bettere0
Value
78.74%e0
Comparator
commercial pesticide thiodiazole coppere0

Not reportedTaxon

Verbatim

e0

“compound 3r could clearly reduce the white pyogenic exudates triggered by Psa infection and afforded excellent control efficiencies of 79.42% (protective activity) and 78.74% (curative activity) at 200 μg/mL, which were quite better than those of commercial pesticide thiodiazole copper”

✓ located verbatim in the source · abstract, characters 1008–1294 · show in text ↑

silicon atom · organism · Oryza sativa (rice)Positive and negative results

20 papers: 18 positive, 2 negative or no effect

17 papers in the same direction as this paper · 2 in the opposite direction

  1. negative
  2. no effect
  3. positive

16 papers more in this group

See all 20 papers →

Claims are grouped by organism, treatment and what was measured or targeted. A paper counts as positive when any of its claims in the group is positive.