Ici Americas, Inc.

Stauffer Chemical Company

Imperial Chemical Industries Limited

Other

Keith H Brownell

Don R Baker

Charles Kezerian

Francis H Walker

Novel fungicidal pyridyl cyclopropane carboxamidines having the general structural formula ##STR1## and tautomers thereof wherein R is selected from the group consisting of hydrogen, pyridyl, substituted pyridyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.6 alkyl, acyl, carbamoyl, sulfonyl and cyano;

Fungicidal pyridyl cyclopropane carboxamidines

Novel fungicidal pyridyl carboximides having the general structural formula ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, preferably methyl;

Fungicidal N-pyridyl imides

Fungicidal pyridyl imidates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are -Cl, -Br, -F and -NO.sub.2, furfuryl pyridyl, C.sub.1 -C.sub.6 alkoxyl substituted thiophosphorus, and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring, R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.2 is selected from the group consisting of methyl and hydrogen, and X is S or O; and fungicidally acceptable organic and inorganic salts thereof.

Fungicidal pyridyl imidates

Novel fungicidal pyridyl amides carboxamides having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl, benzyl, substituted benzyl wherein the substitutions are selected from the group of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkanoyl, halogen, --NO.sub.3 and C.tbd.N, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkenyl and alkanoyl;

Fungicidal pyridyl amides

Novel fungicidal pyridyl cyclopropane carboxamides having the general structural formula ##STR1## wherein R is selected from the group consisting of haloalkyl, preferably C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, and arylalkyl wherein the preferred aryl is phenyl, the alkyl is C.sub.1 -C.sub.3 alkyl and the preferred substitutions are Cl, Br, F and nitro, alkanoyl, preferably C.sub.1 -C.sub.4 alkanoyl, ##STR2## wherein R.sub.3 and R.sub.4 can be alkyl, alkanoyl, alkoxycarbanoyl, benzyl, pyridyl and substituted pyridyl, and when R.sub.3 and Rhd 4 are alkyl together with --N they can form a heterocyclic ring such as piperidine, R.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, preferably methoxy or halomethoxy and halogen wherein the halogen is chlorine, bromine or fluorine, R.sub.2 is hydrogen or methyl, and fungicidally acceptable organic and inorganic salts thereof which are highly effective fungicides for use both as preventive and curative fungicides are disclosed herein. These compounds provide excellent control of fungal growth.

Fungicidal N-(substituted thio)-pyridyl cyclopropane carboxamides

Novel fungicidal pyridyl cyclopropane carboxamidines having the general structural formula ##STR1## and tautomers thereof wherein

Novel fungicidal pyridyl iminocarbonates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are --Cl, --Br, --F and --NO.sub.2 ; furfuryl, pyridyl, C.sub.1 -C.sub.6 alkyl substituted phosphorus, alkanoyl, alkoxycarbonyl, aroyl, preferably benzoyl, alkylthioarbonyl, alkylthioalkyl, alkoxyalkyl, alkoxybenzyl and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring;

Fungicidal pyridyl iminocarbonates

Novel fungicidal pyridyl sulfenyl carbamates having the formula ##STR1## wherein R is selected from the group consisting of haloalkyl, C.sub.1 -C.sub.8 alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, alkanoyl, alkylamino, arylamino, arylalkylamino and substituted pyridylcarbamoyl;

Fungicidal pyridyl sulfenyl carbamates

Novel fungicidal pyridyl cyclopropane carboxamides having the general structural formula ##STR1## wherein R is selected from the group consisting of cycloalkyl, preferably cyclopropyl, hydrogen, alkyl, haloalkyl, substituted alkyl, aryl, substituted aryl, heteroalkyl, alkenyl, OR.sub.1, SR.sub.1 and ##STR2## wherein n is 0-10, preferably 0-2, and R.sub.1 is C.sub.1 -C.sub.4 alkyl, and R.sub.2 is selected from the group consisting of halogen such as chlorine, fluorine and bromine, preferably chlorine, C.sub.1 -C.sub.3 alkoxy such as propoxyethoxy and methoxy, preferably methoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.3 is selected from the group consisting of hydrogen and methyl, X is --O or --S and Y is --O or --S; and fungicidally acceptable organic and inorganic salts thereof which are highly effective fungicides for use both as preventive and curative fungicides are disclosed herein.

Fungicidal pyridyl cyclopropane carboximides

Novel fungicidal pyridyl cyclopropane carboxamides having the general structural formula ##STR1## in which R is selected from the group halogen C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.1 is selected from the group of --H and --C.tbd.N; and R.sub.2 is selected from the group of --H, 1--CH.sub.3 and 2--CH.sub.3 ; X is O or S; and fungicidally acceptable organic and inorganic salts thereof. These compounds provide excellent control of fungal growth.

Fungicidal pyridyl cyclopropane carboxamides

Novel fungicidal pyridyl imidates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl, substituted aryl and arylalkyl wherein the substituents are --Cl, --Br, --F and --NO.sub.2, furfuryl pyridyl, C.sub.1 -C.sub.6 alkyl substituted phosphorus, and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring, R.sub.1 is selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy and C.sub.1 -C.sub.3 haloalkoxy, R.sub.2 is selected from the group consisting of methyl and hydrogen, and X is S or O; and fungicidally acceptable organic and inorganic salts thereof.

Novel fungicidal carbanilates having the general structural formula ##STR1## wherein R is methoxy or allyloxy; R.sub.1 is selected from the group consisting of hydrogen, C.sub.2 -C.sub.4 alkoxyalkyl and formyl; and R.sub.2 is C.sub.1 -C.sub.6 alkyl, preferably C.sub.2 -C.sub.3 alkyl which are highly effective fungicides are disclosed herein.

Fungicidal carbanilates

Novel fungicidal pyridyl cyclopropane carboxamides having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy and halogen; and R.sub.1 is C.sub.1 -C.sub.6 haloalkyl; and fungicidally acceptable organic and inorganic salts thereof.

Fungicidal N-pyridyl haloamides

Novel fungicidal pyridyl iminocarbonates having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 -C.sub.16 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 substituted alkenyl, C.sub.3 -C.sub.4 carboalkoxyalkyl, aryl, arylalkyl having C.sub.1 -C.sub.3 alkyl , substituted aryl and arylalkyl wherein the substituents are --Cl, --Br, --F and --NO.sub.2 ; furfuryl, pyridyl, C.sub.1 -C.sub.6 alkyl substituted phosphorus, alkanoyl, alkoxycarbonyl, aroyl, preferably benzoyl, alkylthioarbonyl, alkylthioalkyl, alkoxyalkyl, alkoxybenzyl and ##STR2## wherein R.sub.3 and R.sub.4 are C.sub.1 -C.sub.10 alkyl and can form a heterocyclic ring;

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San Jose, CA, United States of America

Keith H Brownell