Nihon Bayer Agrochem, K.k.

Niron Bayer Agrochem K.k.

Shin-ichi Narabu

Akihiko Yanagi

Yukiyoshi Watanabe

Toshio Goto

Seishi Ito

Chieko Ueno

Hidenori Hayakawa

Natsuko Minegishi

Tatsuya Yamaoka

Kazuhiro Ukawa

The invention is related to a novel phenylacetylene derivates of formula:

Phenylacetylene derivatives

The invention is related to a novel phenylacetylene derivates of formula: ##STR1## wherein X represents hydrogen, halogen, optionally substituted C.sub.1-6 alkyl; Y represents hydrogen, halogen, cyano, nitro, optionally substituted C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.3-8 cycloalkoxy, optionally substituted C.sub.1-6 alkylthio, C.sub.3-8 cycloalkylthio, C.sub.1-6 alkylsulfinyl, optionally substituted C.sub.1-6 alkylsulfonyl, C.sub.3-8 cycloalkylsulfonyl, C.sub.1-6 alkylsulfonyloxy, optionally substituted sulfonamide, optionally substituted carboxamide, etc., or Y may form together with Z which is bonded to the vicinal carbon atom a 5- or 6-membered ring; n is 0 or 1; Z represents hydrogen or halogen; m is 1 or 2; R represents hydrogen, halogen, C.sub.1-6 alkyl, tri(C.sub.1-6 alkyl)silyl, COOR.sup.c or CONR.sup.d R.sup.e ; Q represents a heterocyclic group, and their use as herbicid.

1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.

Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones

Novel herbicidal tetrazolinone derivatives of the formula ##STR1## and intermediates therefor of the formula ##STR2## wherein R.sup.1 is alkyl substituted by halogen, and

Tetrazolinones

Selective herbicidal tetrazolinones of the formula ##STR1## wherein X is hydrogen or halogen, Y is hydrogen or C.sub.1-4 alkyl, R.sup.1 is C.sub.1-4 alkyl, and R.sup.2 is cycloheptyl or cyclooctyl. and synergistic mixtures thereof.

Herbicidally active tetrazolinones

Novel herbicidal tetrazolinones of the formula ##STR1## wherein Y is hydrogen, bromine or methyl,

Herbicidal tetrazolinones combined with other herbicides

Herbicidal tetrazolinones

1-Substituted-5(4H)-tetrazolinones of the formula (I) ##STR1## wherein R is alkyl, haloalkyl, cycloalkyl, phenyl, substituted phenyl or aralkyl, are obtained in very good yields by reacting, in a polar solvent, an isocyanate of the formula R-NCO (II) with sodium azide (NaN.sub.3) in a molar ratio of 1:1 and in the presence of aluminum chloride (AlCl.sub.3), followed by the addition of water and a mineral acid in excess.

Process for the production of 1-substituted-5(4H)-tetrazolinones

A process for the preparation of a 1-substituted-5(4H)-tetrazolinone of the formula ##STR1## wherein R.sub.1 is defined in the specification n is 0, 1, 2, 3 or 4, which comprises reacting a 1-substituted-5(4H)-tetrazolinethione of the formula ##STR2## with an ethylene oxide of the formula ##STR3## wherein R.sup.2 represents hydrogen, methyl or ethyl, in the presence of a base and in the presence of water, an alcohol or a mixture thereof.

Process for the preparation of 1-substituted-5(4H)-tetrazolinones

Compositions comprising herbicidal tetrazolinones of the formula (I) ##STR1## wherein X is chlorine or bromine, Y is hydrogen, chlorine, bromine, methyl or ethyl, and

Tetrazolinones as herbicides for use in paddy

Herbicidal novel tetrazolinones of the formula ##STR1## wherein Y represents hydrogen, chlorine, or methyl,

Novel tetrazolinones of the formula (I) ##STR1## wherein X is chlorine or bromine,

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Ibaraki, Japan

Shin-ichi Narabu