Rohm and Haas Company

Other

The United States of America As Represented by the Secretary of

Dow Agrosciences LLC

Ronald Ross, Jr

Steven H Shaber

Enrique Luis Michelotti

Anne Ritchie Egan

Willie Joe Wilson

Ted Tsutomu Fujimoto

Edward Michael Szapacs

Duyan Vuong Nguyen

Ted Tsutomo Fujimoto

David Hamilton Young

Robert A Moreau

Steve Howard Shaber

Richard Andrew Slawecki

Fungicidal and insecticidal benzyloxy cyclopropyl substituted aromatic compounds

Certain cyclopropyl oxime ethers substituted by aryl and heterocyclic moieties possess broad spectrum fungicidal and insecticidal properties. These compounds are disclosed along with compositions containing these compounds and methods for controlling fungi and insects by the use of a fungitoxic or insecticidal amount of these compounds.

Aryl and heteroarylcylopropyl oxime ethers and their use as fungicides and insecticides

Compounds with fungicidal properties having formula I ##STR1## where m and n are 0 or 1 provided that m+n is 1; X is hydrogen, halo, (C.sub.1 -C.sub.4)alkyl, or (C.sub.1 -C.sub.4)alkoxy; R is an optionally-substituted alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, aryl, aralkyl, or heterocyclic group; R.sub.1 and R.sub.2 are hydrogen, optionally-substituted alkyl, cycloalkyl, cyano, carboxy alkyl, or aryl; at least one of R.sub.1 and R.sub.2 is hydrogen; and R.sub.3 is alkyl or haloalkyl.

Benzyloxy substituted aromatics and their use as fungicides

Compounds with fungicidal and insecticidal properties having formula I ##STR1## wherein W is ##STR2## n is 0 or 1; Y is O, S, NR.sub.1, or R.sub.6 ;

Dihydropyridazinones and pyridazinones and their use as fungicides and

Compounds with fungicidal properties are presented having the formula ##STR1## wherein m and n are 0 or 1; X is hydrogen, halo, (C.sub.1 -C.sub.4)alkyl or alkoxy; Z is (C.sub.1 -C.sub.12) alkyl or haloalkyl; R, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are independently hydrogen, a halogen, lower alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, arylcycloalkyl, or heterocyclyl, optionally substituted with one or more halogen atoms.

Substituted cyclopropyl phenoxymethyl phenyl carbamates and their use as

Compounds with fungicidal and insecticidal properties having formula ##STR1## wherein X is N or CH; Z is O, S or NR.sub.8 ; A is hydrogen, halo, cyano, (C.sub.1 -C.sub.12)alkyl, or (C.sub.1 -C.sub.12)alkoxy; R.sub.1 and R.sub.8 are independently hydrogen or (C.sub.1 -C.sub.4)alkyl; R.sub.2 is hydrogen, (C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, aryl, aralkyl, heterocyclic, heterocyclic(C.sub.1 -C.sub.4)alkyl or C(R.sub.10).dbd.N--OR.sub.9 ; R.sub.3 is hydrogen, (C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, aryl, aralkyl, aryl(C.sub.3 -C.sub.7)cycloalkyl, heterocyclic or heterocyclic(C.sub.1 -C.sub.4)alkyl; R.sub.4 and R.sub.5 are independently hydrogen, (C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, halo, cyano, (C.sub.1 -C.sub.4)alkoxycarbonyl, aryl, aralkyl, aryl(C.sub.3 -C.sub.7)cycloalkyl, heterocyclic or heterocyclic(C.sub.1 -C.sub.4)alkyl; R.sub.6 is hydrogen, (C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, halo, cyano, (C.sub.1 -C.sub.4)alkoxycarbonyl, aryl, aralkyl, aryl(C.sub.3 -C.sub.7)cycloalkyl, heterocyclic or heterocyclic(C.sub.1 -C.sub.4)alkyl; R.sub.7 is aryl, aralkyl, heterocyclic or heterocyclic(C.sub.1 -C.sub.4)alkyl; R.sub.9 is hydrogen, (C.sub.1 -C.sub.12,)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, (C.sub.1 -C.sub.4)alkylcarbonyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, aryl, or aralkyl; and R.sub.10 is hydrogen, (C.sub.1 -C.sub.12)alkyl, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.8)alkenyl, halo(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, halo(C.sub.2 -C.sub.8)alkynyl, aryl, aralkyl, heterocyclic, or heterocyclic(C.sub.1 -C.sub.4)alkyl.

Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides

Compounds with fungicidal properties are presented having the formula ##STR1## wherein m and n are 0 or 1; X is hydrogen, halo, C.sub.1 -C.sub.4) alkyl or alkoxy; Z is (C.sub.1 -C.sub.12) alkyl or haloalkyl; R, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are independently hydrogen, a halogen, lower alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, arylcycloalkyl, or heterocyclyl, optionally substituted with one or more halogen atoms.

Compounds with fungicidal properties having formula I ##STR1## wherein W is CH.sub.3 --O--A.dbd.C(-)--CO(V)CH.sub.3 ;

Pyridazinones and their use as fungicides

A process for novel sphingolipids and other secondary sphingosine-based compounds is provided which comprises the culturing of an appropriate fungus, harvesting mycelium from the fungus and isolating the sphingolipid from the mycelium. The sphingosine-based materials inhibit protein kinase C, provide an anti-inflammatory effect or provide an anti-tumor effect; furthermore, these sphingosine-based materials provide protection for plants against pathogenic microorganisms.

Sphingolipids and a process thereto

Compounds with fungicidal and insecticidal properties having formula ##STR1## wherein A is N or CH; V is O or NH; m and n are the integers 0 and 1, provided that m+n is 0 or 1; X is independently selected from hydrogen, halo, (C.sub.1 -C.sub.4)alkyl, and (C.sub.1 -C.sub.4)alkoxy; R is independently selected from hydrogen, (C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxy, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.12)alkenyl, (C.sub.2 -C.sub.12)alkynyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.2 -C.sub.12)alkenyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.2 -C.sub.12)alkynyl, (C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.12)alkenyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.12)alkynyl(C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.2 -C.sub.12)alkenyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.12)alkoxy(C.sub.2 -C.sub.12)alkynyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.12)alkenyl(C.sub.3 -C.sub.7)cycloalkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.2 -C.sub.12)alkynyl(C.sub.3 -C.sub.7)cycloalkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.2 -C.sub.12)alkenyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.2 -C.sub.12)alkynyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkoxy(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkenyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkyl(C.sub.1 -C.sub.12)alkoxy(C.sub.1 -C.sub.12)alkynyl(C.sub.3 -C.sub.7)cycloalkyl, aryl, aralkyl, aryl(C.sub.3 -C.sub.7)cycloalkyl, aryl(C.sub.3 -C.sub.7)cycloalkyl(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkylaryl, aryl(C.sub.1 -C.sub.4)alkyl(C.sub.3 -C.sub.7)cycloalkyl, heterocyclic, aryl(C.sub.1 -C.sub.4)alkylheterocyclic heterocyclic(C.sub.1 -C.sub.4)alkyl, heterocyclic(C.sub.3 -C.sub.7)cycloalkyl and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently selected from hydrogen, halogen, (C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxy, halo(C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.12)alkenyl, (C.sub.2 -C.sub.12)alkynyl, (C.sub.3 -C.sub.7)cycloalkyl, cyano, carboxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, aryl, and when taken together R.sub.2 and R.sub.3 form a (C.sub.3 -C.sub.7)cycloalkyl ring, provided that when n=0 or 1 and m=0 R and R.sub.1 are not both hydrogen and when A is N and V is NH and n and m are both zero than R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are other than 1 to 3 substituents independently selected from halogen and (C.sub.1 -C.sub.4)alkyl.

Benzyloxy substituted aromatics and their use as fungicides and

Compounds with fungicidal and insecticidal properties having formula ##STR1## wherein A is N or CH; V is O or NH; m and n are independently 0 and 1 provided that m+n is not 2, and U and W are independently O or N;

Compounds with fungicidal and insecticidal properties having formula I ##STR1## wherein A is N or CH; V is O or NH; m and n are integers 0 and 1 provided that m+n is 1;

This invention relates to substituted dihydropyridazinones, pyridazinones and related compounds, of the formula ##STR1## wherein A, Q, D and R1 are as defined within, compositions containing these compounds and methods of controlling agricultural and mammalian fungal diseases.

Growing community of inventors

Jamison, PA, United States of America

Ronald Ross, Jr