6-bromo-8-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione | 77395-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-bromo-8-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
• 英文别名: 6-Bromo-8-methyl-2,4-dihydro-1h-3,1-benzoxazine-2,4-dione；6-bromo-8-methyl-1H-3,1-benzoxazine-2,4-dione
• CAS: 77395-09-6
• 化学式: C₉H₆BrNO₃
• mdl: MFCD11107022
• 分子量: 256.056
• InChiKey: IHPKGISNXMRMIH-UHFFFAOYSA-N

物化性质

• 密度：
  1.720±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-8-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-氨基-5-溴-3-甲基苯甲酰肼
  参考文献：
  名称：

  新型的以二酰基肼桥为有效Ca 2+调节剂的邻氨基苯甲酰胺二酰胺类似物的合成和杀虫活性的研究

  摘要：

  邻氨基苯甲酰胺是一类针对ryanodine受体（RyRs）的杀虫剂。为了发现针对RyRs的有效杀虫剂，设计并合成了一系列带有二酰基肼桥的新型邻氨基苯甲酰胺。对它们的杀虫活性进行了评估，并总结了初步的构效关系（SAR）。尤其是，化合物5g在浓度为5 mg / L时对东方粘虫（Mythimna separata）表现出良好的杀伤力。钙成像实验结果表明，化合物5g通过破坏Mythimna separata（Walker）和Mythimna separata（Walker）中的钙动态平衡，可作为有效的昆虫Ca 2+水平调节剂。Spodoptera exigua（Hübner），可能激活了ER膜上的RyRs。

  DOI：

  10.1111/cbdd.13349
• 作为产物：
  描述：

  2-氨基-3-甲基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-bromo-8-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
  参考文献：
  名称：

  Synthesis and Bioactivity Study of 2-Acylamino-Substituted N′-Benzylbenzohydrazide Derivatives

  摘要：

  The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using H-1 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (El MS), and their biological activities at a concentration of 600 mg L-1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of <90 mg L-1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at RI play crucial roles in the biological activities of the compounds.

  DOI：

  10.1021/jf303376t

文献信息

• [EN] PROCESS FOR PREPARING N-SUBSTITUTED 1H-PYRAZOLE-5-CARBONYLCHLORIDE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS 1H-PYRAZOLE-5-CARBONYLCHORURES N-SUBSTITUÉS
  申请人：BASF SE

  公开号：WO2013024007A1

  公开（公告）日：2013-02-21

  The present invention relates to a process for preparing an N-substi- tuted 1 H-pyrazole-5-carbonylchloride compound of the formula (I) comprising the steps of i) deprotonating a compound of the formula (II) with a base selected from lithium-organic base having a carbon or nitrogen bound lithium or with a magnesium-organic base having a carbon bound magnesium; and ii) subjecting the product obtained in step (i) to a chlorocarbonylation by reacting it with a reagent selected from the group consisting of phosgene or a phosgene equivalent, to obtain a compound of formula (I).

  本发明涉及一种制备式(I)N-取代1H-吡唑-5-羰基氯化物的过程，包括以下步骤：i) 用选择自碳或氮与锂结合的有机锂碱或碳与镁结合的有机镁碱的碱去质子化式(II)化合物；和ii) 将步骤(i)中获得的产物经氯羰基化反应，与磷酰氯或磷酰氯等效物中选择的试剂反应，以获得式(I)化合物。
• [EN] ANILINE TYPE COMPOUNDS<br/>[FR] COMPOSÉS DE TYPE ANILINES
  申请人：BASF SE

  公开号：WO2013024008A1

  公开（公告）日：2013-02-21

  The present invention relates to compounds of the formula (I) wherein R1 and R2 independently of one another are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl or together represent an aliphatic chain, or the like; R3 is halogen, cyano, C1-C8-alkyl, C1-C8- haloalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C1-C8-alkoxy, phenyl, or the like; R4 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C3-C8- cycloalkyl, C3-C8-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, phenyl, or the like; t is 0 or 1; p is 0, 1, 2, 3 or 4. The present invention also relates to a process for preparing a compound of the formula (I) which comprises reacting a compound of the formula (II) with a compound of the formulae (III) or (IV): where t, p, R1 R3, R3 and R4 are as defined in any of claims 1 to 6 and where A- is an equivalent of an anion having a pΚB of at least 10 (determined under standard conditions in water).

  本发明涉及以下式(I)的化合物，其中R1和R2彼此独立地为氢、C1-C10-烷基、C1-C10-卤代烷基、C3-C10-环烷基、C3-C10-卤代环烷基、C2-C10-烯基、C2-C10-卤代烯基或者一起代表一个脂肪链等；R3为卤素、氰基、C1-C8-烷基、C1-C8-卤代烷基、C3-C8-环烷基、C3-C8-卤代环烷基、C2-C8-烯基、C2-C8-卤代烯基、C1-C8-烷氧基、苯基等；R4为氢、C1-C10-烷基、C1-C10-卤代烷基、C3-C8-环烷基、C3-C8-卤代环烷基、C2-C10-烯基、C2-C10-卤代烯基、苯基等；t为0或1；p为0、1、2、3或4。本发明还涉及一种制备上述式(I)化合物的方法，包括将式(II)的化合物与式(III)或(IV)的化合物反应：其中t、p、R1、R3、R3和R4如权利要求1至6中的任一所定义，A-是至少在水中标准条件下具有至少10的pΚB值的阴离子的当量。
• Synthesis, Insecticidal Activities, and Structure–Activity Relationship of Phenylpyrazole Derivatives Containing a Fluoro-Substituted Benzene Moiety
  作者：Yangyang Zhao、Li Gao、Huangong Li、Pengwei Sun、Fanfei Meng、Yan Zhang、Yongtao Xie、Binqiao Sun、Sha Zhou、Yi Ma、Lixia Xiong、Na Yang、Yuxin Li、Zhengming Li

  DOI：10.1021/acs.jafc.9b08090

  日期：2020.10.7

  Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted

  氟化有机化合物代表了一个日益重要的商业化学品家族。将氟引入活性成分已成为开发现代农作物保护产品的有效途径。考虑到氟的特殊性质以及二酰胺类杀虫剂的高效性和选择性，我们设计并合成了27种含有氟代苯基吡唑的邻氨基苯甲酰胺类类似物。初步的生物测定表明，大多数目标化合物对分离的Mythimna separata和Plutella xylostella具有良好的生物学活性。含有2,4,6-三氟取代苯环的化合物IIIf在0.1 mg L –1时显示出对分离支原体的杀虫活性为43％，而对照中的氯蒽醌含量为36％。IIIe在10 –5 mg L –1时对小菜蛾的活性为94％，而对照为70％。因此，将氟引入二酰胺杀虫剂中对于增加活性是有用的。昆虫电生理研究表明，IIIf可以提高分离的第三个分离支原体幼虫神经细胞中的钙浓度，这进一步证实了赖多碱受体（RyR）是其潜在的靶标。
• Synthesis, insecticidal activity, and structure–activity relationship (SAR) of anthranilic diamides analogs containing oxadiazole rings
  作者：Yuhao Li、Hongjun Zhu、Kai Chen、Rui Liu、Abdalla Khallaf、Xiangning Zhang、Jueping Ni

  DOI：10.1039/c3ob40345a

  日期：——

  anthranilic diamides analogs (3–11, 16–24) containing 1,2,4- or 1,3,4-oxadiazole rings were synthesized and characterized by 1H NMR, MS and elemental analyses. The structure of 3-bromo-N-(2-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)-4-chloro-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (18, CCDC-924454) was determined by X-ray diffraction crystallography. The insecticidal activities against

  一系列氨茴酸二酰胺类似物（的3-11，16-24含有1,2,4-或1,3,4-恶二唑环）的合成和表征通过1 H NMR，MS和元素分析。的结构3-溴-N-（2-（3-（4-溴苯基）-1,2,4-恶二唑-5-基）-4-氯-6-甲基苯基）-1-（3-氯吡啶-2-基）-1 H-吡唑-5-羧酰胺（18，CCDC-924454）通过X射线衍射晶体学测定。评价了对小菜蛾和甜菜夜蛾的杀虫活性。结果表明，大多数标题化合物显示出良好的杀幼虫活性对小菜蛾，尤其是化合物3-溴-N-（4-氯-2-甲基-6-（5-（甲硫基）-1,3,4-恶二唑-2-基）苯基）-1-（3-氯吡啶-2-基） -1 H-吡唑-5-羧酰胺（6），其显示对71.43％的活性小菜蛾在0.4微克毫升-1和抵抗33.33％甜菜夜蛾以1μg毫升-1。结构-活性关系表明，用1,3,4-恶二唑修饰的化合物比用1,2,4-恶二唑修饰的化合物更有效，连接在
• [EN] PROCESS FOR PREPARING N-SUBSTITUTED 1H-PYRAZOLE-5-CARBOXYLATE COMPOUNDS AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN COMPOSÉ N-1 H-PYRAZOLE SUBSTITUÉ-5-CARBOXYLATE ET DE SES DÉRIVÉS
  申请人：BASF SE

  公开号：WO2013076092A1

  公开（公告）日：2013-05-30

  The present invention relates to a process for preparing an N-substituted 1 H-pyrazole- 5- carboxylate compound of the formula (l-A) comprising the steps of i) deprotonating a compound of the formula (II) in which the variables R1, R2 and r are each as defined in the description and the claims, with a magnesium-organic base having a carbon bound magnesium; and ii) subjecting the product obtained in step (i) to a carbonylation by reacting it with a reagent selected from the group consisting carbon dioxide or a carbon dioxide equivalent, to obtain a compound of formula (l-A); and it relates to further conversions to yield a N-substituted 1H-pyrazole-5-carbonyl chloride compound of the formula (I).

  本发明涉及一种制备式(l-A)的N-取代1 H-吡唑-5-羧酸酯化合物的过程，包括以下步骤：i) 用具有碳键镁的镁有机碱去质子化式(II)的化合物，其中变量R1、R2和r如描述和索赔中定义，并ii) 将步骤(i)中得到的产物经过羰基化反应，与选择自二氧化碳或二氧化碳等效物的试剂反应，得到式(l-A)的化合物；并且涉及进一步的转化以产生式(I)的N-取代1H-吡唑-5-羰基氯化物化合物。