Abstract
Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is a promising target for herbicide discovery. Search for new compounds with novel chemotypes is a key objective for agrochemists. Here, we describe the discovery and systematic SAR-based structure optimization of novel N-isoxazolinylphenyltriazinones 5–9 as PPO inhibitors. The in vivo herbicidal activity and in vitro Nicotiana tabacum PPO (NtPPO) inhibitory activity were explored in detail. A number of the new synthetic compounds displayed strong PPO inhibitory activity with Ki values in the nanomolar range. Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375–37.5 g ai/ha by postemergence application and showed improved monocotyledonous weed control compared to saflufenacil. Most promisingly, ethyl 3-(2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 5a, with a Ki value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (Ki = 10 nM) and trifludimoxazin (Ki = 31 nM), respectively. Moreover, 5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5–75 g ai/ha. Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application, indicating that 5a could be a potential herbicide candidate for weed control in paddy fields.
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Claims 8
Claim · model-written summary
Some new synthetic N-isoxazolinylphenyltriazinones displayed strong PPO inhibitory activity with Ki values in the nanomolar range.
Verbatim
e0“A number of the new synthetic compounds displayed strong PPO inhibitory activity with Ki values in the nanomolar range”
Claim · model-written summary
Some of the compounds gave excellent, broad-spectrum weed control at 9.375–37.5 g ai/ha applied postemergence.
Verbatim
e0“Some compounds exhibited excellent and broad-spectrum weed control at the rate of 9.375–37.5 g ai/ha by postemergence application”
Claim · model-written summary
The compounds showed improved control of monocotyledonous weeds compared with saflufenacil.
Verbatim
e0“showed improved monocotyledonous weed control compared to saflufenacil”
Claim · model-written summary
Compound 5a, with a Ki of 4.9 nM, was over 2-fold more potent than saflufenacil (Ki = 10 nM).
Verbatim
e0“5a, with a Ki value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (Ki = 10 nM) and trifludimoxazin (Ki = 31 nM), respectively”
Claim · model-written summary
Compound 5a, with a Ki of 4.9 nM, was 6-fold more potent than trifludimoxazin (Ki = 31 nM).
Verbatim
e0“5a, with a Ki value of 4.9 nM, displayed over 2- and 6-fold higher potency than saflufenacil (Ki = 10 nM) and trifludimoxazin (Ki = 31 nM), respectively”
Claim · model-written summary
Compound 5a gave excellent, broad-spectrum control of 32 kinds of weeds at 37.5–75 g ai/ha.
Verbatim
e0“5a showed excellent and broad-spectrum weed control against 32 kinds of weeds at 37.5–75 g ai/ha”
Claim · model-written summary
Rice showed relative tolerance to compound 5a applied postemergence at 150 g ai/ha.
- Taxon
- Rice
Oryza sativae0 - Treatment
- 5a at 150 g ai/ha by postemergence applicatione0
- Outcome
- relative tolerancee0
Not reportedComparatorDirection
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“Rice exhibited relative tolerance to 5a at 150 g ai/ha by postemergence application”
Claim · model-written summary
The authors conclude that 5a could be a potential herbicide candidate for weed control in paddy fields.
- Taxon
- RiceOryza sativae1
- Outcome
- potential herbicide candidate for weed control in paddy fieldse0
Organisms pictured · Representative pictures of the matched species, not figures from the paper.
Verbatim
e0“indicating that 5a could be a potential herbicide candidate for weed control in paddy fields”
e1“Rice”
The same questions in other papers
herbicide · disease · Oryza sativa (rice)Positive and negative results
16 papers in the same direction as this paper · 7 in the opposite direction
- positive
- negative
- no effect
20 papers more in this group
See all 24 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.