- Synthesis of some O, O-diethylphosphoric acid thioesters
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We synthesized a number of O,O-diethyl S-(ω-ethylmercaptoalkyl) thiophosphates, and their methyl methosulfates and ethyl ethosulfates.
- Yarv,Aaviksaar,Lobanov,Godovikov
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- Lewis Acid Promoted Aerobic Oxidative Coupling of Thiols with Phosphonates by Simple Nickel(II) Catalyst: Substrate Scope and Mechanistic Studies
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Exploring new catalysts for efficient organic synthesis is among the most attractive topics in chemistry. Here, using Ni(OAc)2/LA as catalyst (LA: Lewis acid), a novel catalyst strategy was developed for oxidative coupling of thiols and phosphonates to phosphorothioates with oxygen oxidant. The present study discloses that when Ni(OAc)2 alone was employed as the catalyst, the reaction proceeded very sluggishly with low yield, whereas adding non-redox-active metal ions such as Y3+ to Ni(OAc)2 dramatically promoted its catalytic efficiency. The promotional effect is highly Lewis acidity dependent on the added Lewis acid, and generally, a stronger Lewis acid provided a better promotional effect. The stopped-flow kinetics confirmed that adding Y(OTf)3 can obviously accelerate the activation of thiols by Ni(II) and next accelerate its reaction with phosphonate to generate the phosphorothioate product. ESI-MS characterizations of the catalyst disclosed the formation of the heterobimetallic Ni(II)/Y(III) species in the catalyst solution. Additionally, this Ni(II)/LA catalyst can be applied in the synthesis of a series of phosphorothioate compounds including several commercial bioactive compounds. This catalyst strategy has clearly supported that Lewis acid can significantly improve the catalytic efficiency of these traditional metal ions in organic synthesis, thus opening up new opportunities in their catalyst design.
- Xue, Jing-Wen,Zeng, Miao,Zhang, Sicheng,Chen, Zhuqi,Yin, Guochuan
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p. 4179 - 4190
(2019/04/30)
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- Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations
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New late-stage phosphorothiolation methods are disclosed that allow the efficient transfer of SP(O)(OR)2 groups to diversely functionalized substrates using nucleophilic and electrophilic reagents. The nucleophilic reagent, tetramethylammonium O,O-dimethyl phosphorothioate, was synthesized in near-quantitative yield from Me3SiP(O)(OMe)2, elemental sulfur and Me4NF. Its umpolung with N-bromophthalimide provided the electrophilic reagent, O,O-dimethyl-S-(N-phthalimido)phosphorothioate. Complementary methods based on these reagents enable the phosphorothiolation of diversely functionalized alkyl halides, arenediazonium salts, arylboronic acids and electron-rich arenes in good yields under mild conditions. (Figure presented.).
- Kovács, Szabolcs,Bayarmagnai, Bilguun,Aillerie, Alexandre,Goo?en, Lukas J.
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supporting information
p. 1913 - 1918
(2018/03/30)
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- Cs2CO3-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes
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An efficient Cs2CO3-catalyzed oxidative coupling of thiols with phosphonates and arenes that uses molecular oxygen as the oxidant is described. These reactions provide not only a novel alkali metal salt catalyzed aerobic oxidation, but also an efficient approach to thiophosphates and sulfenylarenes, which are ubiquitously found in pharmaceuticals and pesticides. The reaction proceeds under simple and mild reaction conditions, tolerates a wide range of functional groups, and is applicable to the late-stage synthesis and modification of bioactive molecules.
- Song, Song,Zhang, Yiqun,Yeerlan, Adeli,Zhu, Bencong,Liu, Jianzhong,Jiao, Ning
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supporting information
p. 2487 - 2491
(2017/02/23)
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- A thiophosphate synthetic method of compound and the method in a plurality of pharmaceutical application in the synthesis of (by machine translation)
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The invention discloses a having the general formula (III) of the thiophosphate synthetic method of compound, the purpose is to provide a novel, condition is simple, easy to industrial production of the thiophosphate synthetic method of compound. The method is to have the general formula (I) of the organophosphorus oxygen apperception compound having the general formula (II) with a mercaptan or phenyl-sulfhydryl apperception compound mixed, under the effects of catalyst, obtained by the reaction of the formula (III) of the thiophosphate compound. The method of the invention, can be cheap efficient synthesis of thiophosphate compounds, in actual production will have extensive application prospect. (by machine translation)
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Paragraph 0239; 0240; 0241; 0242
(2017/07/20)
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- Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives
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The invention relates to novel cis-alkoxyspiro-substituted tetramic acid derivatives of the formula (I), in which A, G, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly cis-alkoxyspiro-substituted tetramic acid derivatives and secondly a crop plant compatibility-improving compound.
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- SUBSTITUTED SPIROCYCLIC KETOENOLS
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The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
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- Aryl-substituted heterocyclic enaminones
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The invention relates to novel heterocyclic enaminones of the general formula (I) in which Ar, Z, K, X, y1, Y2, Y3, Y4, Y5, Y6 and V are as defined in the description, to their use as herbicides, acaricides and insecticides, and to processes for their preparation.
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- Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms
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The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.
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- Optically active 2,5-bisaryl-delta1-pyrrolines and their use as pest control agents
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Novel optically active Δ1-pyrrolines of the formula (I) in which R1, R2, R1, R4, and m are each as defined in the description, a plurality of the processes for preparing these substances and their use for controlling pests.
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- Phenyl-substituted 5,6-dihydrophyne derivatives for use as pesticides and herbicides
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The present invention relates to novel phenyl-substituted 5,6-dihydro-pyrone derivatives of the formula (I) in which W, X, Y, Z, G, A, B, Q1 and Q2 are each as defined in the description, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
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- Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms
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Novel pyrazolylbiphenylcarboxamides of the formula (I) in which R1, R2, X, m, Y and n are each as defined in the description, a plurality of processes for preparing these substances and their use for controlling undesirable microorganisms, and also novel intermediates and their preparation.
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- Triazolopyrimidines
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The invention relates to novel triazolopyrimidines of the formula 1wherein X represents halogen, Y represents a hydrogen atom or halogen, and R has the meanings given in the disclosure, to a process for the preparation of the new compounds, and to their use as microbicides.
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- Delta1-pyrrolines used as pesticides
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Novel Δ1-pyrrolines of the formula (I) in which Ar1, Ar2 and Q are each as defined in the description, a plurality of processes for preparing these substances and their use for controlling pests.
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- Delta 1-pyrrolines used as pesticides
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Novel Δ1-pyrrolines of the formula (I) in which R1, R2, R3, m and Q have the meanings given in the description, a plurality of processes for preparing these substances and their use for controlling pests.
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- Triazolopyrimidines
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Novel triazolopyrimidines of the formula in which R1, R2, R3 and X have the meanings given in the description, a process for preparing these novel substances and their use for controlling undesirable microorganisms and animal pests. Novel amines of the formula in which R4 has the meanings given in the description, and processes for their preparation.
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- Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)
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The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.
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- Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)
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The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 2 to 10, n represents 0, 1 or 2, Y represents unsubstituted or substituted methylene and p represents 1, 2 or 3. and to processes for their preparation and to their use as pesticides.
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- Isothiazolecarboxamides and their use as microbicides
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Isothiazolecarboxamides of the formula: wherein X, Y, R1, R2, R3 and R4 have the meanings given in the specification, may be used as microbicides.
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- Isothiazolecarboxylic acid derivatives and their use as microbicides
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Novel isothiazolecarboxylic acid derivatives of the formula (I), in which A, Q, Z and k have the meanings mentioned in the specification, processes for the preparation of the new compounds and their use as microbicides.
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- Substituted imide derivatives
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The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.
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- Pyrazolyl benzyl thioethers
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The invention relates to novel pyrazolyl benzyl thioethers, to two processes for their preparation and to their use for controlling harmful organisms.
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- Pyrazolyl benzyl ethers
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The invention relates to novel pyrazolyl benzyl ethers, to a process for their preparation and to their use for controlling harmful organisms.
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- Thienyl-pyrazoles and their use for controlling pests
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The present invention relates to compounds of the formulae (Ia) and (Ib) wherein R1represents C1-10alkyl which may be unsubstituted or substituted with halogen, or represents C2-4alkoxyalkyl, C2-4hydroxyalkyl, C3-6cycloalkyl, hydroxy, C1-9alkoxy which may be unsubstituted or substituted with halogen, or represents C3-6cycloalkoxy, C2-4alkoxyalkoxy or C3-4alkynyloxy, and R2represents hydrogen, C1-4alkoxycarbonyl, C1-3alkylcarbonyl or C2-4alkoxyalkyl, to processes for their preparation and to their use for controlling animal pests.
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- Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides
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The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.
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- Phenyl substituted 4-hydroxy tetrahydroxypyridone
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The present invention relates to novel compounds of the formula (I) in which W, X, Y, Z, G, A, B, Q1, Q2 and D are each as defined in the description, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
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- Active substance combinations having insecticidal and acaricidal properties
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The invention relates to insecticidal mixtures, comprising compounds of the formula (I) in which W, X, Y, Z, A, B, D and G are each as defined above and agonists or antagonists of nicotinic acetylcholine receptors for protecting plants against attack by pests.
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- Pyrazolyl benzyl ether deriviatives having a fluoromethoxy group and the use thereof as pesticides
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The invention relates to novel pyrazolyl benzyl ethers, to a process for their preparation and to their use for controlling harmful organisms.
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- Use of riboflavin and flavin derivatives as chitinase inhibitors
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The invention relates to the use of riboflavin and of flavin derivatives with chitinase-inhibitory action for controlling arthropods, nematodes and chitin-containing fungi.
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- SUBSTITUTED N-BENZOYL-N'(TETRAZOLYLPHENYL)-UREAS AND THEIR USE AS PEST CONTROL AGENTS
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The present invention relates to new substituted N-benzoyl-N′-(tetrazolylphenyl)-ureas of the formula (I) in which R1, R2, R3, R4 and n are as stated in the description, to processes for their preparation, and to their use as pesticides.
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- Heterocylic fluoroalkenyl thioethers and the use thereof as pesticides (IV)
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The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which m represents integers from 3 to 10, n represents 0, 1 or 2 and Het represents the following, in each case optionally substituted, groupings: and to processes for their preparation and to their use as pesticides.
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- Heterocyclic fluoroalkenyl thioethers (II)
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The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Het represents the groupings, where R1 represents hydrogen, mercapto, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkenyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, Y represents oxygen or sulphur, and R2 represents hydrogen, alkyl or optionally substituted aryl, and to processes for their preparation and to their use as pesticides.
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- Sulphonyltriazol derivatives and their use for combating micro-organisms
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Novel sulphonyltriazole derivatives of the formula in which Hal represents fluorine, chlorine or bromine, R1represents hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy or represents optionally substituted heterocyclyl and R2represents alkyl or represents optionally substituted heterocyclyl or represents a radical of the formula in which R3represents halogen, alkyl or phenyl, R4represents hydrogen or alkyl and R5represents alkyl or optionally substituted phenyl, or R4and R5together with the nitrogen atom to which they are attached form a heterocyclic ring which may be substituted and which may also contain an additional heteroatom, a process for preparing these substances and their use for controlling undesirable microorganisms.
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- Phenyl-substituted cyclic enaminones
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The present invention relates to novel phenyl-substituted cyclic enaminones of the formula (I): in which Ar, X, Z, Y, K, n and m are each as defined in the description, to a plurality of processes and intermediates for their preparation and to their use as herbicides and pesticides.
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- Methoximinophenylacetic acid amides
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The invention relates to novel methoximinophenylacetamides, to a process for their preparation and to their use as fungicides.
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- Diphenylimidazolines
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The invention relates to novel diphenylimidazolines of the formula (I) in which Ar1, Ar2and R are each as defined in the description, and a plurality of processes for their preparation and to their use for controlling animal pests.
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- Phenylacetic acid heterocyclyl amides having an insecticidal effect
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Novel phenylacetic acid heterocyclyl amides of the formula in which R1, R2, R3, R4, A, X and n are as defined in the description, a process for preparing these novel compounds and their use for controlling undesirable microorganisms and animal pests. Novel intermediates of the formula and a plurality of processes for their preparation.
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- Arylphenyl-substituted cyclic keto-enols
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The present invention relates to novel arylphenyl-substituted cyclic ketoenols of the formula (I) in whichX represents halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogeno-alkoxy, halogenoalkenyloxy, nitro, cyano or in each case optionally substituted phenyl, phenoxy, phenylthio, phenyl-alkoxy or phenylalkylthio,Y represents in each case optionally substituted cycloalkyl, aryl or hetaryl,Z represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,CKE represents one of the groups ?in whichA, B, D, G and Q1 to Q6 are each as defined in the description, to a plurality of processes for their use as pesticides and herbicides.
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- Sulfonyl benzazolones
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Sulphonylbenzazolones of the formula in whichR1, R2, R3, R4, R5 and Q are each as defined in the description.a process for preparing these compounds and their use as microbicides in crop protection and in the protection of materials.
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- Selective Sulfur Oxygenation in Phosphoroamidate, Thionophosphate, and Thiophosphate Agrochemicals by Perfluoro-cis-2,3-dialkyloxaziridine
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Several organophsophorus agrochemicals 2a-g with thioether, phosphoramidic, phosphorothioic, and phosphorothionic functions were reacted with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 1.The selective oxygenation of sulfide function to give sulfoxide derivatives 3a-g occured in high yields without overoxidation to sulfone products.Sulfoxides 3a-e were further oxidized under mild conditions to the corresponding sulfones 4a-e.All the products are themselves of interest as analytical environmental standards and their preparation is described in detail.
- Terreni, Marco,Pregnolato, Massimo,Resnati, Giuseppe,Benfenati, Emilio
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p. 7981 - 7992
(2007/10/02)
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