Nippon Soda Co., Ltd.

Mikio Sawaki

Hisao Ishikawa

Isao Iwataki

Yoshihiko Hirono

Shozo Yamada

Yasushi Yasuda

Masashi Nakajima

Kiyoshi Katsuura

Mitsuo Asada

Takashi Okabe

Kuniyasu Maeda

Daigaku Takiguchi

Tadashi Kyotani

Kenji Suzaki

Tsutomu Kaku

Akira Kaneko

Nobuo Tomita

Method for the preparation of unsaturated ketones

There is provided a method for the production of hydroxylamine derivatives or the salt thereof in which a salt of hydroxamic acid is reacted with an alkylating agent such as diethyl sulfate to form an ester of hydroxamic acid, which is reacted with mineral acid in an aqueous solution of lower alcohol so as to prepare hydroxylamine derivatives or the salt thereof. In this process, the incorporation of an oxidizing agent or aldehydes in the reaction system will significantly reduce the content of nitrosoamines in the resulting solution of hydroxylamine derivatives or the salt thereof. Therefore, the resulting hydroxylamine derivatives obtained with a lesser content of harmful compound will be useful as an intermediate for the production of drugs and pesticides.

Method for the production of hydroxylamine derivatives

.alpha., .beta.-unsaturated-ketones are synthesized by reacting with an aldehyde and an alkali metal salt of acetoacetic acid in the presence of an aliphatic secondary amine in the mixture of heterogeneous solvents producing an oil layer and a water layer.

Synthesis of .alpha., .beta.-unsaturated-ketones

Various substituted cyclohexane-1,3-diones are useful as herbicides. An exemplary species is 2-[1-(allyloxyamino)propylidene]-5,5-dimethylcyclohexane-1,3-dione.

Cyclohexane derivatives

A compound of the general formula ##STR1## WHEREIN R.sub.1 is lower alkyl having six or less carbon atoms,

Substituted cyclohexene esters

A compound of the general formula ##STR1## wherein R.sub.1 is lower alkyl,

Oxacyclohexane derivatives

A compound of the formula ##SPC1## Wherein

2-Cyclohexene-1-one derivatives

A compound of the formula ##SPC1## Wherein X is hydrogen or halogen:

Herbicidal composition of 3,4-dihydro-2H-pyrane-2,4-diones and methods

Compounds of the formula ##SPC1## Wherein R.sub.1 and R.sub.2 are alkyl having 2 to 6 carbon atoms or phenyl; R.sub.3 is alkyl having 1 to 10 carbon atoms, alkenyl or alkynyl having up to six carbon atoms; R is alkyl of 1 to 20 carbon atoms, phenyl or phenyl substituted with halogen, methyl, methoxy or nitro; and A is carbonyl or sulfonyl, are effective as herbicides, plant growth regulators and fungicides.

.alpha.-Pyrone derivatives

Various substituted cyclohexane-1,3-diones are useful as herbicides. An exemplary species is 2-[1-(allyloxyamino)propylidene]5,5-dimethylcyclohexane-1,3-dione.

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Odawara, Japan

Mikio Sawaki