Studies of the New Herbicide KIH-6127. Part III. Synthesis and Structure-Activity Studies of Analogues of KIH-6127 against Barnyard Grass (Echinochloa oryzicola)*

Tamaru, Masatoshi; Masuyama, Naoshi; Sato, Masahiro; Takabe, Fumiaki; Inoue, Jun; Hanai, Ryo

doi:10.1002/(sici)1096-9063(199701)49:1<76::aid-ps491>3.0.co;2-e

Cited by 9 publications

(2 citation statements)

References 11 publications

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“…in 1996 (Tokyo, Japan;Tamaru and Saito, 1996). Tamaru et al (1997) reported that (E), isomer (I), has been confirmed to restrain the plant enzyme acetolactate synthase (ALS) and prevent branched chain amino acid biosynthesis, and the (E), or pyriminobac-methyl (EPM), showed stronger soil adsorption and weaker hydrophilic properties than (Z), or pyriminobac-methyl (ZPM); thus, EPM was selected as the best compound to develop a commercial weedicide, which is commonly used to control the growth of sedges and both gramineous and annual weeds. The chemistry of EPM is well understood; the octanol-water partition coefficient is 2.31 (low) at pH 7 and 20 • C, the solubility in the water is 9.25 mg L −1 (low) at 20 • C, and the vapor pressure is just 3.1 × 10 −5 Pa (low) at 20 • C (Lewis et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Environmental behaviors of (E) pyriminobac-methyl in agricultural soils

Zhou

Jia

et al. 2022

SOIL

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Abstract. E or pyriminobac-methyl (EPM), a pyrimidine benzoic acid esters herbicide, has a high potential as weedicide; nevertheless, its environmental behaviors are still not well understood. In this study, we systematically investigated, for the first time, the adsorption–desorption, degradation, and leaching behaviors of EPM in agricultural soils from five exemplar sites in China (Phaeozems – S1; Anthrosol – S2; Ferralsol – S3; Alisol – S4; Plinthosol – S5) through laboratory simulation experiments. Our results show that the EPM adsorption–desorption results were well fitted by the Freundlich model (R2>0.9999). In the analyzed soils, the Freundlich adsorption (i.e., Kf ads) and desorption (i.e., Kf des) coefficients of EPM varied between 0.85 and 32.22 mg1-1/n L1/n kg−1 and 0.78–5.02 mg1-1/n L1/n kg−1, respectively. The mobility of EPM in soils S1–S5 was categorized as immobile, slightly immobile, highly mobile, slightly mobile, and slightly mobile, respectively. Moreover, the degradation of EPM reflected first-order kinetics, where its half-life ranged between 37.46 and 66.00 d, depending on the environmental conditions, and abiotic degradation was predominant in the degradation of this compound. Overall, the high leaching ability and desorption capacity of EPM were accompanied by a low adsorption capacity, and there were no significant relationships between pH and the leaching rate of EPM in the five types of soils. In contrast, the organic matter content, cation exchange capacity, and soil clay content were the main components responsible for the observed leaching rates. We found that EPM degrades easily, has a high adsorption affinity, and a low mobility in S1, which results in a low contamination risk for groundwater systems. On the contrary, this compound degrades slowly in S2, S3, S4, and S5, due to a low adsorption affinity and moderate mobility, which results in a high contamination risk for groundwater systems. Therefore, our results may serve as a reference for evaluating the risks involved in the increasingly wide application of this compound.

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Section: Introductionmentioning

confidence: 99%

Environmental behaviors of (E) pyriminobac-methyl in agricultural soils

Zhou

Jia

et al. 2022

SOIL

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“…In 1996 (Tokyo, Japan) (Tamaru and Saito 1996). Tamaru et al (1997)) reported that (E) -isomer (I) has been confirmed to restrain the plant enzyme acetolactate synthase (ALS) and prevent branched chain amino acid biosynthesis, and the (E) -pyriminobac-methyl (EPM) showed stronger soil adsorption and weaker hydrophilic properties than (Z) -pyriminobac-methyl (ZPM), thus EPM was selected as the best compound to develop a commercial weedicide, which is commonly used to control the growth of sedges and both gramineous and annual weeds.…”

Section: Introductionmentioning

confidence: 99%

Environmental Behaviors of (E)-Pyriminobac-methyl in Agricultural Soils

Zhou

Jia

et al. 2021

Preprint

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(E)-Pyriminobac-methyl (EPM), a pyrimidine benzoic acid esters herbicide, has a high potential as weedicide; nevertheless, its environmental behaviors are still not well understood. In this study, we systematically investigated for the first time the adsorption–desorption, degradation, and leaching behaviors of EPM in agricultural soils from five exemplar sites in China (characterized by different physicochemical properties) through laboratory simulation experiments. The EPM adsorption–desorption results were well fitted by the Freundlich model (R2 > 0.9999). In the analyzed soils, the Freundlich adsorption (i.e., Kf-ads) and desorption (i.e., Kf-des) coefficients of EPM varied between 0.85–32.22 mg1−1/n L1/n kg−1 and between 0.78–5.02 mg1−1/n L1/n kg−1, respectively. Moreover, the degradation of EPM reflected first-order kinetics: its half-life ranged between 37.46–66.00 d depending on the environmental conditions, and abiotic degradation was predominant in the degradation of this compound. The mobility of EPM in the five soils varied from immobile to highly mobile. The groundwater ubiquity score ranged between 0.9765–2.7160, indicating that EPM posed threat to groundwater quality. Overall, the results of this study demonstrate the easy degradability of EPM, as well as its high adsorption affinity and low mobility in soils with abundant organic matter content and high cation exchange capacity. Under such conditions, there is a relatively low contamination risk for groundwater systems in relation to this compound. Overall, our findings provide a solid basis for predicting the environmental impacts of EPM.

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7‐(4,6‐Dimethoxypyrimidinyl)oxy‐ and ‐thiophthalides as novel herbicides: Part 1. CGA 279 233: a new grass‐killer for rice

Lüthy

Zondler

Rapold

et al. 2001

Pest Management Science

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A series of novel types of 7-(4,6-dimethoxypyrimidin-2-yl)oxy- and -thio-3-methyl-1 (3H)-isobenzofuranones were discovered at Dr R Maag AG. From the thio-isobenzofuranyl series, CGA 279 233--BSI-proposed common name pyriftalid--was chosen for further development as a grass herbicide for use in rice. General synthetic approaches to these new phthalic acid-derived compounds are given, with emphasis on the synthesis of pyriftalid and its physico-chemical behaviour.

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Studies of the New Herbicide KIH-6127. Part III. Synthesis and Structure-Activity Studies of Analogues of KIH-6127 against Barnyard Grass (Echinochloa oryzicola)*

Cited by 9 publications

References 11 publications

Environmental behaviors of (<i>E</i>) pyriminobac-methyl in agricultural soils

Environmental behaviors of (<i>E</i>) pyriminobac-methyl in agricultural soils

Environmental Behaviors of (E)-Pyriminobac-methyl in Agricultural Soils

7‐(4,6‐Dimethoxypyrimidinyl)oxy‐ and ‐thiophthalides as novel herbicides: Part 1. CGA 279 233: a new grass‐killer for rice

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Studies of the New Herbicide KIH-6127. Part III. Synthesis and Structure-Activity Studies of Analogues of KIH-6127 against Barnyard Grass (Echinochloa oryzicola)*

Cited by 9 publications

References 11 publications

Environmental behaviors of (&lt;i&gt;E&lt;/i&gt;) pyriminobac-methyl in agricultural soils

Environmental behaviors of (&lt;i&gt;E&lt;/i&gt;) pyriminobac-methyl in agricultural soils

Environmental Behaviors of (E)-Pyriminobac-methyl in Agricultural Soils

7‐(4,6‐Dimethoxypyrimidinyl)oxy‐ and ‐thiophthalides as novel herbicides: Part 1. CGA 279 233: a new grass‐killer for rice

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Environmental behaviors of (<i>E</i>) pyriminobac-methyl in agricultural soils

Environmental behaviors of (<i>E</i>) pyriminobac-methyl in agricultural soils