Carbon—hydrogen spin—spin coupling constants

The invention relates to novel spiroketal-substituted cyclic ketoenols of formula (I), where A, B, Q1, Q2, D, G, W, X, Y, and Z have the given meanings, method and intermediates for production thereof and use thereof as pesticide and/or microbicide and/or herbicide. The invention further relates to selective herbicidal agents, containing the spiroketal-substituted cyclic ketoenols and a compound improving the compatibility with cultivated plants.

Spiroketal-substituted cyclic ketoenols

The invention relates to new compounds of the formula (I) in which W, X, Y, Z and CKE have the meanings given 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, the compounds of the formula (I) and, secondly, at least one crop plant compatibility enhancer compound. The invention relates further to boosting the activity of crop protection compositions comprising compounds of the formula (I) by adding ammonium salts or phosphonium salts and, if appropriate, penetrants.

Biphenyl-substituted spirocyclic ketoenols

Publisher Summary This chapter reviews the chemistry of hydantoins. The hydantoins can be synthesized using amino acids, cyanate or thiocyanate salts, alkyl or aryl isocyanates and isothiocyanates, ureas, α-dicarbonyl compounds, Bucherer–Bergs and Read reactions, and cycloaddition reactions with heterocumulenes. The chapter also illustrates physicochemical studies on hydantoins. H-NMR, IR, and UV techniques are widely used to study ionization and tautomerism in hydantoins. Hydantoins are weak acids which owe their acidic character to dissociation of the proton bonded to the 3-nitrogen atom as this allows for maximum delocalization of charge in anion. The chapter also presents physicochemical studies on hydantoins using ultraviolet spectroscopy, mass spectrometry, infrared spectroscopy, nuclear magnetic resonance spectroscopy, crystal structure determinations, and quantum mechanical calculations. The reactivity of hydantoins and their derivatives are described further in the chapter. Hydantoins and thiohydantoins can react with nucleophilic and electrophilic as well as with other types of reagents. On protonation in a strongly acidic solution, hydantoin cations are formed. Hydantoins can easily be alkylated in the N-3 position by treatment with alkyl halides in an alkaline solution in protic or aprotic solvents. Other alkylating agents include dimethyl sulfate and diazomethane.

The Chemistry of Hydantoins

The invention relates to new aryl phenyl substituted ketoenols of formula (I), where X is halogen, alkyl, alkoxy, alkenyloxy, alkylthio, alkyl sulfinyl, alkyl sulfonyl, halogen alkyl, halogen alkoxy, halogen alkenyloxy, nitro, cyano or possibly substituted phenyl, phenoxy, phenylthio, phenyl alkoxy or phenyl alkylthio; Z is possibly substituted cycloalkyl, aryl or hetaryl; W and Z independently of each other are hydrogen, halogen, alkyl, alkoxy, alkenyloxy, halogen alkyl, halogen alkoxy, halogen alkenyloxy, nitro or cyano; and CKE is one of groups (1), (2), (3), (4), (5), (6), (7) or (8), where A, B, D, G and Q1 to Q6 have the meanings assigned in the description. The invention also relates to several methods for producing said ketoenols and to their use as pest control agents and herbicides.

Aryl phenyl substituted cyclic ketoenols

The spirohydantoin (α-isomer) obtained from 4-tert-butylcyclohexanone by the Bucherer–Bergs reaction has been shown by n.m.r., u.v., and considerations of steric hindrance to have the tert-butyl gr...

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Stereochemistry of the Bucherer–Bergs and Strecker Reactions of 4-tert-Butylcyclohexanone

Stereochemistry of the bucherer-bergs and strecker reactions of 4-tert-butylcyclohexanone