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Dichlormid Sale

(Synonyms: 二氯丙烯胺;烯丙酰草胺) 目录号 : GC63587

Dichlormid 是除草剂安全剂。Dichlormid 上调 ZmGST27 和 ZmMRP1 的表达并增加 ZmGT1。

Dichlormid Chemical Structure

Cas No.:37764-25-3

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1 g
¥315.00
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产品描述

Dichlormid is a herbicide safener. Dichlormid up-regulates expression of ZmGST27 and ZmMRP1 and increases ZmGT1[1][2].

[1]. D P Dixon, et al. Purification, Regulation and Cloning of a Glutathione Transferase (GST) From Maize Resembling the Auxin-Inducible type-III GSTs. Plant Mol Biol. 1998 Jan;36(1):75-87.
[2]. Sen Pang, et al. Co-induction of a glutathione-S-transferase, a Glutathione Transporter and an ABC Transporter in Maize by Xenobiotics. PLoS One. 2012;7(7):e40712.

Chemical Properties

Cas No. 37764-25-3 SDF
别名 二氯丙烯胺;烯丙酰草胺
分子式 C8H11Cl2NO 分子量 208.09
溶解度 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 4.8056 mL 24.0281 mL 48.0561 mL
5 mM 0.9611 mL 4.8056 mL 9.6112 mL
10 mM 0.4806 mL 2.4028 mL 4.8056 mL
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Research Update

Photodegradation of the herbicide EPTC and the safener Dichlormid, alone and in combination

Chemosphere 2002 Mar;46(8):1183-9.PMID:11951984DOI:10.1016/s0045-6535(01)00207-7.

Photodegradation of the herbicide EPTC (S-ethyl-N, N-dipropylthiocarbamate), and the safener Dichlormid (2,2-dichloro-N, N-diallylacetamide) has been examined in methanol and in water solutions. Irradiation of EPTC and Dichlormid with UV light at 254 nm caused rapid degradation in both media. Remarkable and gradual changes in color of EPTC irradiated solution was observed from clear to yellow then to intense orange. EPTC half-life of elimination in water was 14.0, and 18.5 min, and in methanol 37.2 and 32.2 min, when irradiated with and without Dichlormid, respectively. There was significant difference between rate of EPTC degradation in water and methanol in the presence or in the absence of Dichlormid. Negligible degradation of EPTC or Dichlormid at > 290 nm was observed. Photoproducts were separated and identified using GC or/and thin-layer chromatography then identified using mass spectrometry. It appeared that some products have high molecular weight that formed as a result of dimerization. This is possibly a result of the coupling of radicals that formed through EPTC degradation. The cleavage of C-S and C-N bonds accounted for the formation of these radicals. Gradual dealkylation of the acid chains of EPTC has also occurred. EPTC-sulfoxide, EPTC-sulfone, Propylamine and dipropylamine were detected as photoproducts of EPTC at 254 nm. Dichlormid pathways of degradation at 254 nm were characterized as dechlorination, dealkylation, and hydrolysis both in water and methanol. The findings showed that Dichlormid did not significantly affect EPTC photodegradation either at 254 nm or at > 290 nm. The biological/toxicological properties of the photoproducts need further study, particularly the dimer compounds.

Fatty acid elongation is important in the activity of thiocarbamate herbicides and in safening by Dichlormid

J Exp Bot 2003 Apr;54(385):1289-94.PMID:12654880DOI:10.1093/jxb/erg126.

The thiocarbamates, such as pebulate (S-propyl butyl (ethyl) thiocarbamate) are a well-established class of herbicides. They inhibit fatty acid elongation, which is necessary for the biosynthesis of constituents of surface waxes and suberin and this has been proposed to be important for their toxicity. In this study lipid metabolism was investigated in herbicide-treated barley (Hordeum vulgare) and a pernicious weed, wild oats (Avena ludoviciana), to test the hypothesis that inhibitory effects on fatty acid elongation could be counteracted by the safer, Dichlormid. Pebulate and its sulphoxide derivative (thought to be the active metabolite in vivo) were tested against lipid metabolism in barley or wild oat shoots. In both plants there was a significant inhibition of very long chain fatty acid (VLCFA) synthesis at herbicide concentrations > or =25 micro M. The extent to which safener Dichlormid could prevent the inhibition of VLCFA synthesis was different in the two species. Previous treatment of barley with Dichlormid (N,N-diallyl-2,2-dichloroacetamide) enabled fatty acid elongation in the presence of pebulate or pebulate sulphoxide, but had no effect on wild oats. The effects on fatty acid elongation mimicked the differential safening action of Dichlormid observed on shoot elongation and growth in the two species. These data provide further evidence that inhibition of VLCFA formation is important for the mechanism of action of thiocarbamates.

The inhibition of fatty acid elongation by pebulate can be effectively counteracted by the safener Dichlormid

Biochem Soc Trans 2000 Dec;28(6):650-1.PMID:11171157doi

The thiocarbamate herbicide pebulate inhibits fatty acid elongation, which is necessary for surface lipid biosynthesis. As both barley and wild oats are susceptible to pebulate, the safener Dichlormid was used to study the reversal of its herbicidal effect. Fatty acid elongation was restored by a Dichlormid pretreatment in barley, but not in pebulate-expressed oats.

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

Molecules 2020 Oct 28;25(21):4986.PMID:33126493DOI:10.3390/molecules25214986.

The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a-k, 3a-k, and 4a-k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by 1H-NMR, 13C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound Dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than Dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection.

Photochemical Transformations of Dichloroacetamide Safeners

Environ Sci Technol 2019 Jun 18;53(12):6738-6746.PMID:31117539DOI:10.1021/acs.est.9b00861.

Dichloroacetamide safeners are commonly added to commercial chloroacetamide herbicide formulations and widely used worldwide, but their environmental fate has garnered little scrutiny as a result of their classification as "inert" ingredients. Here, we investigated the photolysis of dichloroacetamide safeners to better understand their persistence and the nature of their transformation products in surface waters. High-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy were used to characterize photoproducts. Of the four commonly used dichloroacetamide safeners, only benoxacor undergoes direct photolysis under simulated natural sunlight ( t1/2 ∼ 10 min). Via a photoinitiated ring closure, benoxacor initially yields a monochlorinated intermediate that degrades over longer irradiation time scales to produce two fully dechlorinated diastereomers and a tautomer, which further photodegrade over several days to a structurally related aldehyde confirmed via NMR. Dichlormid, AD-67, and furilazole were more slowly degraded by indirect photolysis in the presence of the photosensitizers nitrate, nitrite, and humic acid. Reactive entities involved in these reactions are likely hydroxyl radical and singlet oxygen based on the use of selective quenchers. These safeners also directly photolyzed under higher energy ultraviolet (UV) light, suggesting their potential transformation in engineered systems using UV for disinfection. The finding that dichloroacetamide safeners can undergo photolysis in environmental systems over relevant time scales demonstrates the importance of evaluating the fate of this class of "inert" agrochemicals.