- NEW APPROACH TO THE SYNTHESIS OF 2,6-DIFLUOROBENZOYL ISOCYANATE AND ITS USE IN THE PREPARATION OF N-(2,6-DIFLUOROBENZOYL)-N'-(POLYFLUOROARYL)UREAS
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The treatment of 2,6-difluorobenzoyl chloride with trimethylsilyl isocyanate gave 2,6-difluorobenzoyl isocyanate.This product reacts with polyfluoroaromatic amines to give the corresponding N-(2,6-difluorobenzoyl)-N'-(polyfluoroaryl)urea, which hold potential as inhibitors for the biosynthesis of insect chitin. Keywords: 2,6-difluorobenzoyl chloride, trimethylsilyl isocyanate, 2,6-difluorobenzoyl isocyanate, polyfluoroaromatic amines, N-(2,6-difluorobenzoyl)-N'-(polyfluoroaryl)ureas, insect chitin biosynthesis inhibitors.
- Odinokov, V. N.,Kukovinets, O. S.,Lozhkina, E. A.,Bikulova, V. Zh.,Petrova, T. D.,et al.
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Read Online
- Synthetic method of diflubenzuron impurities for quantitative and qualitative analysis
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The invention relates to a synthetic method of diflubenzuron impurities for quantitative and qualitative analysis, and belongs to the technical field of pesticide synthesis. The diflubenzuron impurities are synthesized in the following way, wherein R is t
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Paragraph 0049-0052
(2021/06/09)
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- Synthetic method of benzamide pesticide
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To 2, 5 - dichlorophenol is used as a raw material, and an addition step with hexafluoropropylene is sequentially carried out. The method is characterized in that 2, 5 - dichlorophenol (2-5 - SMN), acetonitrile, phenol and sodium carbonate aqueous solutio
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Paragraph 0063-0066
(2021/08/25)
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- Synthetic method of substituted benzoyl isocyanate
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The invention discloses a preparation method of substituted benzoyl isocyanate, and belongs to the field of pesticide/medicine intermediates. Substituted benzoyl chloride and cyanate react in an organic solvent in the presence of a composite catalyst composed of a Lewis acid and p-toluene sulfonic acid to generate substituted benzoyl isocyanate. The method avoids the use of expensive oxalyl chloride, highly toxic phosgene, and the like, inhibits the generation of side reaction and byproduct namely cyanobenzene, selects the reaction conditions suitable for commercialization, enhances the selectivity and yield of the reaction, and reduces the generation of wastes, production cost, and environmental pollution.
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Paragraph 0025-0026
(2020/04/22)
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- Preparation method for fluazuron
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The invention discloses a preparation method for fluazuron in the technical field of organic synthesis. The method comprises the following steps: (1) allowing 2,6-difluorobenzamide to react with oxalyl chloride so as to generate a compound with a formula
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Paragraph 0009; 0028-0029; 0033-0034; 0038-0039
(2020/05/02)
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- Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
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Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.
- Bai, Ping,Cheng, Yao,Lu, Xiaoxia,Yang, Jian,Zhang, Qi,Zheng, Cheng
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p. 5806 - 5815
(2020/06/19)
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- Synthesis method of insecticide teflubenzuron and intermediate 2,6-difluorobenzamide of insecticide teflubenzuron
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The invention discloses a synthesis method of an insecticide teflubenzuron and an intermediate 2,6-difluorobenzamide of the insecticide teflubenzuron, belonging to the field of pesticides. The synthesis method comprises the following steps: step 1, preparation of 2,6-dichlorobenzylidene chloride: preparing turbid liquid of dichlorotoluene and phosphorus pentachloride, introducing chlorine gas, layering materials by utilizing a gas-liquid separator, collecting a crude product, and rectifying the crude product to obtain the 2,6-dichlorobenzylidene chloride; and 2, preparation of 2,6-dichlorobenzonitrile: mixing 2,6-dichlorobenzylidene chloride, acetic acid, zinc chloride, hydroxylamine hydrochloride and sodium acetate, carrying out heating for a reflux reaction, conducting cooling, stirring,filtering and drying successively after the reaction is completed so as to obtain 2, 6-dichlorobenzonitrile. By adopting a one-pot method, a reaction route is shortened, total yield is increased to 67.3% from conventional 55.4%, and cost is greatly reduced.
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- Accessing Difluoromethylated and Trifluoromethylated cis-Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
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Reported here is a straightforward process in which a cyclic (alkyl)(amino)carbene/Rh catalyst system facilitates the preferential addition of hydrogen to the substitution sites of difluoromethylated and trifluoromethylated arenes and heteroarenes, leading to dearomative reduction. This strategy enables the diastereoselective synthesis of cis-difluoromethylated and cis-trifluoromethylated cycloalkanes and saturated heterocycles, and even allows formation of all-cis multi-trifluoromethylated cyclic products with a defined equatorial orientation of the di- and trifluoromethyl groups. Deuterium-labeling studies indicate that hydrogen preferentially attacks the substitution sites of planar arenes, resulting in dearomatization, possibly with heterogeneous Rh as the reactive species, followed by either reversible or irreversible hydrogen addition to the nonsubstitution sites.
- Zhang, Xue,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 16785 - 16789
(2019/11/11)
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- Investigation of novel pesticides with insecticidal and antifungal activities: Design, synthesis and SAR studies of benzoylpyrimidinylurea derivatives
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In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 μg mL?1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 μg mL?1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.
- Chen, Peiqi,Song, Xiangmin,Fan, Yongmei,Kong, Weihao,Zhang, Hao,Sun, Ranfeng
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- Synthetic method for aryl formyl isocyanate
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The invention relates to a preparation method, and mainly relates to a synthetic method for aryl formyl isocyanate, which includes: (1) dropwise adding an aryl formamide solution, dissolved in an organic solvent, to a bis(trichloromethyl)carbonate solution; (2) slowly heating the mixture to a high temperature of 60-180 DEG C, and at the temperature, completely dropwise adding the rest of the bis(trichloromethyl)carbonate to the solution in the step (1) within 0.5-5 h, and then continuously performing the reaction for 1-6 h, after the reaction is finished, recycling the organic solvent, and performing pressure-reduced distillation to the organic solvent to prepare the aryl formyl isocyanate. The method overcome the problems of poor safety and high investment cost due to use of oxalyl chloride or carbonyl chloride in the prior art. The method has reasonable processes, is environment-friendly, low-cost, safe and reliable, is high in yield of the aryl formyl isocyanate, is low in generation of waste water, waste gas and solid wastes, and is suitable for industrial production.
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Paragraph 0019
(2019/01/07)
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- Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds
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A wide range of chemicals such as amides, hydrazides, amines, alcohols, carbazate, and sulfonate were reacted with acyl isocyanates generated by the reaction of primary amides with oxalyl chloride to give symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds. This method provides means for convenient one-pot, two-step synthesis of compounds bearing urea, carbamate, and other functional groups from cheap and commercially available starting reagents. It is expected that the results presented in this report will expand the medicinal chemist’s toolbox.
- Hernandez, Anolan Garcia,Grooms, Gregory M.,El-Alfy, Abir T.,Stec, Jozef
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p. 2163 - 2176
(2017/05/05)
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- Synthesis method of chlorfluazuron and application of chlorfluazuron in insecticide preparation
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The invention belongs to the technical field of pesticide preparations, particularly relates to a synthesis method of chlorfluazuron and further discloses an application of chlorfluazuron in insecticide preparation. According to the synthesis method of chlorfluazuron, chlorfluazuron is prepared from 2,3-dichloro-5-(trifluoromethyl)pyridine, 2,6-dichloro-4-aminophenol and 2,6-difluorobenzoyl isocyanate as synthetic raw materials and N,N-dimethylacetamide as a reaction solvent on the basis of a conventional synthesis route in the prior art; under the action of a ZSM molecular sieve based catalyst, not only can synthesis of chlorfluazuron be realized, but also a reaction can be performed with the same reaction solvent, so that the problem of complicated process caused by the fact that solvents are required to be recovered step by step during two-step synthesis of chlorfluazuron in the prior art is solved; compared with the technology in the prior art, the synthesis method of chlorfluazuron has the advantages that the synthesis yield of products is further increased and product content is higher.
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Paragraph 0041; 0043; 0044
(2017/07/21)
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- Azobenzene-benzoylphenylureas as photoswitchable chitin synthesis inhibitors
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Benzoylphenylureas (BPUs) are used as synthetic insect growth regulators for inhibiting chitin synthesis. Merging insecticidal BPUs with photoswitchable azobenzene generated photoresponsive chitin synthesis inhibitors. A prepared azobenzene-benzoylphenylurea can be activated upon irradiation with UV light, and shows 6-fold and 2-fold activity difference to armyworm (Mythimna separata) and German cockroach (Blattella germanica) sulfonylurea receptors, respectively. This is the first example of a photoswitchable BPU insecticide. The generation of such a photoresponsive BPU insecticide allows for modulation of the insecticidal activity by light, and may facilitate the spatiotemporal control over the sulfonylurea receptor and the mechanistic study of this kind of insecticide.
- Tian, Xue,Zhang, Chao,Xu, Qi,Li, Zhong,Shao, Xusheng
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supporting information
p. 3320 - 3323
(2017/04/21)
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- Method for preparing isocyanate by using amine and carbonyl fluoride
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The invention discloses an efficient synthesis method for preparing corresponding isocyanate by enabling carbonyl fluoride to directly react with amine. The efficient synthesis method mainly comprises the following two steps: carrying out acylation reaction on the amine and the carbonyl fluoride according to a preferable proportion in an anhydrous inertial organic solvent under a sealed environment and a proper reaction condition, thus generating an intermediate-carbamyl fluoride; (2) carrying out dehydrofluorination on the intermediate-carbamyl fluoride under normal pressure and the proper reaction condition, thus obtaining the target isocyanate. During a reaction process, addition of a catalyst is not needed, the reaction conditions are mild, excessive carbonyl fluoride and a used solvent during the reaction process can be efficiently recycled and reused, and a by-product HF can be commercially sold after being collected and refined.
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Paragraph 0083-0084
(2017/07/07)
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- Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
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To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
- Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun
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supporting information
p. 2544 - 2546
(2016/07/07)
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- Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety
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A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.
- He, Haifeng,Wang, Xiaoyan,Shi, Liqiao,Yin, Wenyan,Yang, Ziwen,He, Hongwu,Liang, Ying
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supporting information
p. 3263 - 3270
(2016/07/12)
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- A seed of common peganum alkali nenzoyl urea compound, and its preparation method and application
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The invention discloses banisterine benzoyl urea compounds and a preparation method and application thereof. The banisterine benzoyl urea compounds have a structural formula I shown in the specification; in the formula I, R1 can be methyl, phenyl, 3,4,5- triethoxy phenyl, p-methoxyphenyl or p-chlorphenyl, R2 can be H or Br, and X can be O or S. The banisterine benzoyl urea compounds have an outstanding insecticidal activity for Culex fatigans, prodenia litura and Chilo suppressalis; a part of the compounds are identical to a control insecticide Dibenzoyl-1-tert-butylhydrazine in term of activity; the banisterine benzoyl urea compounds have good inhibitory activity for rice sheath blight disease, alternaria solani, Collectotrichum musae, grey mould fruit rot of strawberry and sour rot pathogenic bacteria of citrus; a part of the compounds have better inhibitory activity for the above five phytopathogens than validamycin. The banisterine derivatives are simple in structure and easy to synthesize; the synthesis process is simple, the product purity is high; the banisterine benzoyl urea compounds and the preparation method thereof are suitable for large-scale industrial popularization and application.
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Paragraph 0077; 0078
(2016/10/09)
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- Synthesis and antitumor activity of novel N-benzoyl-N'-substituted pyrimidinyl (thio)semicarbazide derivatives
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A series of substituted pyrimidinyl (thio)semicarbazide derivatives were designed and synthesized. The antitumor results showed that the activity of thiosemicarbazide compounds (series II) was generally higher than that of the corresponding semicarbazide derivatives (series I). Among them, IIk displayed higher cytotoxicity against HL-60, BGC-823 and Bel-7402 than that of adriamycin and exhibited broad in vitro cytotoxicity against 13 human tumor cell lines. Meanwhile, the cytotoxic selectivity and anti-multidrug resistance were evaluated, and IIk exhibited selective cytotoxicity against cancer cells in comparison to human normal cells and had significant anti-multidrug resistance capability. The bioassay results showed that IIk showed great promise as a potent lead compound for further antitumor discovery.
- Song, Gaopeng,Li, Jianzuo,Tian, Hao,Li, Yasheng,Hu, Dekun,Li, Ying,Cui, Zining
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p. 329 - 334
(2016/04/04)
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- Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2- furanmethyl ester
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Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.
- Ying,Bao-Ju,Ling,Miao, Hong-Jian,Yan-Xia,Yang, Xin-Ling
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scheme or table
p. 3037 - 3042
(2011/07/31)
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- Synthesis, crystal structure and bioactivities of N-(2,6-difluorobenzoyl)- N′-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea
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N-(2,6-difluorobenzoyl)-N′-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl] urea, 3, has been synthesized by reaction of 2-amino-5-(pyrid-4-yl)-1,3,4- thiadiazole with 2,6-difluorobenzoyl isocyanate, and its structure was characterized with X-ray crystallographic,
- Song, Xin-Jian,Tan, Xiao-Hong,Wang, Yan-Gang
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p. 479 - 482
(2008/09/20)
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- A novel class of potent influenza virus inhibitors: Polysubstituted acylthiourea and its fused heterocycle derivatives
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A series of polysubstituted and fused heterocycle derivatives of acylthiourea was prepared and the biological activity against influenza virus was evaluated. Of the analogues that demonstrated IC50s 0.1 μM, acylthiourea derivatives 16 and 50 were further investigated as candidates with the most potential for future development. The SAR of these compounds are discussed and they represent a novel class of highly potent and selective inhibitors of influenza virus.
- Sun, Chuanwen,Huang, Hai,Feng, Meiqing,Shi, Xunlong,Zhang, Xiaodong,Zhou, Pei
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p. 162 - 166
(2007/10/03)
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- Benzoylphenylurea insecticides and methods of using them to control cockroaches
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Compounds of formula (I): wherein R1 is H or F and R2 is CF3 or CF2CF3, exhibit unexpectedly superior activity against cockroaches and are also useful to control other insects.
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- Synergistic juvenoid chitin synthesis inhibitor termiticide compositions
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Combinations of a chitin synthesis inhibitor (e.g. hexaflumuron, flufenoxuron, lufenuron, and dimiin) with a juvenile hormone mimic (e.g. methoprene and pyriproxyfen) afford synergistic activity against termites.
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- 2-chloro-3, 5-bis(trifluoromethyl)phenyl benzoyl urea derivative and process for preparing the same
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PCT No. PCT/KR97/00123 Sec. 371 Date Dec. 21, 1998 Sec. 102(e) Date Dec. 21, 1998 PCT Filed Jun. 25, 1997 PCT Pub. No. WO98/00394 PCT Pub. Date Jan. 8, 1998The present invention relates to a novel benzoyl urea derivative which exhibits potent growth-retar
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- Development of a Class-Specific Competitive ELISa for the Benzoylphenylurea Insecticides
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A competitive enzyme-linked immunosorbert assay (ELISA) was developed for the quantitative detection of five benzophenylurea insecticides in soil (90% methanol extraction) and water. No significant matrix effects were observed. Conjugates of diflubenzuron derivatives with proteins were prepared by attachment at either the urea nitrogen of diflubenzuron or the 4-position of the aniline ring, wherein bridging groups of various lengths were used between the hapten and the protein carrier. All combinations of antiserum to each immunogen and enzyme tracer were examined, and an assay was developed using an antibody developed to a hapten conjugate coupled through a succinyl chain at the 4-aniline position. The assay gave 50% inhibition of antibody binding (IC50) at 0.6 ppb for diflubenzuron, 5 ppb for teflubenzuron, 10 ppb for flufenoxuron, 31 ppb for lufenuron, and 45 ppb for chlorfluazuron, with detection limits in the range of 0.05-2.3 ppb for these compounds. The basis for the superior cross-reaction of diflubenzuron was examined by molecular modeling, which suggested that the planarity of the molecules, electron-withdrawing groups, and steric effects of chlorines attached to the phenyl ring may be critical factors affecting antibody binding.
- Wang, Shuo,Allan, Robin D.,Skerritt, John H.,Kennedy, Ivan R.
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p. 3330 - 3338
(2007/10/03)
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- Ozonolysis of Alkenes and Studies of the Reactions of Polyfunctional Compounds. LVIII. Ozonolysis of 2,6-Difluoro-β,β-Dimethylstyrene as an Effective Way to 2,6-Difluorobenzamide and Synthesis of New Analogs of Difluorobenzurone
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Ozonolysis of 2,6-difluoro-β,β-dimethylstyrene, formed by isomerization of the product of alkylation of sodium derivative of m-difluorobenzene with methallyl chloride, yields 2,6-difluorobenzamide, transformation of which to 2,6-difluorobenzoyl isocyanate and the reaction of the latter with corresponding arylamines leads to new effective analogs of difluorobenzurone.
- Odinokov,Ishmuratov,Kukovinets,Harisov,Lozhkina,Mustafin,Abdrahmanov,Tolstikov
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p. 202 - 204
(2007/10/03)
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- Method of preparing acylisocyanates
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The invention relates to a novel process for the preparation of acyl isocyanates which consists in reacting oxalyl chloride with an N-trialkylsilylcarboxamide or an N,N-bis(trialkylsilyl)carboxamide. The process makes it possible to obtain acyl isocyanates in good yield, in particular acyl isocyanates derived from aliphatic amides, and under simplified reaction conditions.
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- Pesticidal heterocyclic compounds
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Compounds of the general formula: wherein R1 represents a hydrogen or halogen atom; R2 represents a halogen atom; R3 represents a hydrogen or halogen atom or an alkyl group; R4 and R5 each independent
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- Synthesis and anthelmintic activity of 3'-benzoylurea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
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Reaction of 3-amino derivatives of the nematocides tetramisole and levamisole with variously substituted benzoylisocyanates gave a series of benzoylureas I which were tested for activity against helminths and ectoparasites. Compounds bearing 2,6-difluoro and 4-trifluoromethyl substituents had potent nematocidal activity in both mice and sheep. No antiectoparasitic activity was observed.
- Weikert,Bingham Jr.,Emanuel,Fraser-Smith,Loughhead,Nelson,Poulton
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p. 1630 - 1633
(2007/10/02)
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- Process for the preparation of acyl isocyanates
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The invention relates to a process for the preparation of acyl isocyanates of formula STR1 in which R is an alkyl radical, a substituted or unsubstituted naphthyl or phenyl radical or a substituted or unsubstituted aromatic heterocyclic radical, which con
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- CONDENSATION OF ACYL CHLORIDE ON SODIUM CYANATE : PREPARATION OF ACYL ISOCYANATES
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The catalytic effects of various metal halides and solvents on the reaction of benzoyl chloride with sodium cyanate were studied.It has been found that SnCl4, and ZnCl2 catalyze the reaction to give the corresponding acyl isocyanates in good yields.The scope of the reaction was studied and a number of aroyl isocyanates and their derivatives were prepared.A few non aromatic isocyanates and their derivatives were also prepared.
- Deng, M. Z.,Caubere, P.,Senet, J. P.,Lecolier, S.
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p. 6079 - 6086
(2007/10/02)
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- N-(2,6-Difluorobenzoyl-N-'-(2-fluoro-4-halophenyl)urea
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A urea derivative of the general formula, STR1 (wherein X is a halogen), which has higher insecticidal activity than known similar compounds, with lowered toxicity to mammals and fishes. The derivative can be produced by reacting 2-fluoro-4-haloaniline with 2,6-difluorobenzoyl isocyanate or reacting 2-fluoro-4-halo-phenylisocyanate with 2,6-difluorobenzamide.
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- Urea derivatives and pesticidal compositions containing same
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This invention relates to compounds of the formula STR1 Z' is chlorine or fluorine, with the proviso that Z' is chlorine when Q is the moiety of Formula III. The invention also relates to the preparation of the compounds, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds as active ingredients.
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- Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds
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Novel substituted N-pyrrolylphenyl-N'-benzoylurea compounds of the formula STR1 in which X and Y independently of one another are each hydrogen or halogen, R is hydrogen or halogen, and Z is hydrogen, halogen or methyl. The compounds have valuable propert
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- N-(2H-Difluoro-3,5-dichloro-phenyl)-N'-(2,6-difluorobenzoyl) urea derivative and pesticidal compositions containing same
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This invention relates to compounds of the formula STR1 wherein STR2 X is oxygen or sulfur; Y is chlorine or fluorine; and Z is hydrogen, chlorine, or fluorine, as well as to the preparation thereof, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds of Formula I as active ingredients.
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- Insecticidal bicyclooxyphenyl ureas
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Novel bicyclooxyphenyl ureas, such as 1-(bicyclooxyphenyl)-benzoyl ureas, are provided which exhibit pesticidal activity. The compositions are conveniently prepared by reacting an isocyanate with either an amide or a bicyclooxyaniline.
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- N-Benzoyl N'-pyridyloxy phenyl urea
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N-benzoyl N'-pyridyloxy phenyl ureas having the formula STR1 wherein X represents a halogen atom; R represents a C1 -C4 alkyl group and n is 0, 1 or 2 are useful as insecticides.
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- Oxadiazindione derivatives useful as insecticides
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Insectically active oxadiazindione derivatives of the formula: STR1 wherein R1 is 2-chlorophenyl, 4-chlorophenyl, 2,6-dichlorophenyl, 3,5-dichlorophenyl, 2,6-difluorophenyl, 3-nitrophenyl, 3-trifluoromethylphenyl, 2-tolyl or 3,5-xylyl, and R2 is phenyl or phenyl substituted by methyl, methoxy, chlorine, fluorine, or nitro, provided that at least one of R1 and R2 is a chloro-or fluoro-substituted phenyl group.
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