Studies of the New Herbicide KIH-6127. Part I. Novel Synthesis of Methyl 6-Acetylsalicylate as a Key Synthetic Intermediate for the Preparation of 6-Acetyl Pyrimidin-2-yl Salicylates and Analogues

Tamaru, Masatoshi; Saito, Yoshihiro

doi:10.1002/(sici)1096-9063(199606)47:2<125::aid-ps394>3.3.co;2-o

Cited by 5 publications

(8 citation statements)

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“…Among them, methoxy compound (1) exhibited the highest activity. Cyano (2), methylthio (3), nitro (4) and thiocyano (5) analogues also exhibited excellent herbicidal activity in this order. Carboxylic acid derivatives, such as (6) and 7, and the alkyl(aryl)oxy compounds such as (8), (9), (10), (11) and 12exhibited moderate herbicidal activity.…”

Section: Lead Compound Generationmentioning

confidence: 85%

Synthesis and Structure-activity Relationships of Herbicidal Thiophene Sulfonylurea Compounds

et al. 1997

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In a study of sulfonylurea herbicides, we found that some thiophene sulfonylureas, substituted at the 3 position and possessing the sulfonylurea bridge at the 2 position of the thiophene ring, exhibit high herbicidal activities on paddy field application. Although most of them are phytotoxic to rice (Oryza sativa), introduction of a fluorine atom onto the substituent attached at the 3 position of the thiophene moiety improved the selectivity to rice. Namely, N-{(4, 6-dimethoxypyrimidin-2-yl)aminocarbonyl}-3-{(2, 2, 2-trifluoroethoxy)methyl}-2-thiophenesulfonamide and N-{(4, 6-dimethoxypyrimidin-2-yl)-aminocarbonyl}-3-{(2-fluoroethoxy)methyl}-2-thiophene sulfonamide were selected as good herbicides for paddy field application.

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Section: Lead Compound Generationmentioning

confidence: 85%

Synthesis and Structure-activity Relationships of Herbicidal Thiophene Sulfonylurea Compounds

et al. 1997

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“…The title compound was synthesized according to the literature procedure of Tamaru & Saito (1996). Crystals appropriate for data collection were obtained by slow evaporation of an isopropyl ether solution at 298 K.…”

Section: Methodsmentioning

confidence: 99%

“…The title compound, (I) ( Fig. 1), is a key intermediate in the synthesis of pesticides such as the herbicide KIH-6127 (Tamaru & Saito, 1996). In this paper, we report the results of an X-ray diffraction study of this compound, as its monohydrate.…”

Section: Commentmentioning

confidence: 97%

Methyl 2-benzyloxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate monohydrate

2005

Acta Cryst E

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“…S1), is composed of a mixture of its (E) -isomer (I) and (Z) -isomer (II) as the active ingredient due to its chemical structure contain oxime (Song et al 2010), a mixture of two isomers (I and II) in a > 9:1 (major/minor) ratio which was developed from sulfonylurea by Kumiai Chemical Industry Co., Ltd. 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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Studies of the New Herbicide KIH-6127. Part I. Novel Synthesis of Methyl 6-Acetylsalicylate as a Key Synthetic Intermediate for the Preparation of 6-Acetyl Pyrimidin-2-yl Salicylates and Analogues

Cited by 5 publications

References 0 publications

Synthesis and Structure-activity Relationships of Herbicidal Thiophene Sulfonylurea Compounds

Synthesis and Structure-activity Relationships of Herbicidal Thiophene Sulfonylurea Compounds

Methyl 2-benzyloxy-6-(2-methyl-1,3-dioxolan-2-yl)benzoate monohydrate

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

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