Ciba-geigy Corporation

Fmc Corporation

Janssen Pharmaceutica Nv

Ciba-giegy Corporation

Peter Riebli

Adolf Hubele

Wolfgang Eckhardt

Walter Kunz

Helmut Zondler

Hanspeter Fischer

Rudolph C Thummel

Roger G Hall

Joachim Lorenz

Reinhardt Grade

Protected phosphine oxides of formula X are useful intermediates for the preparation of tertiary phosphine oxides and acylphosphine oxide photoinitiators. ##STR1##

Protected phosphine oxides

A process for the preparation of a protected phosphine oxide which comprises reacting a phosphinate ester having a protecting group on the phosphorus atom with an organomagnesium halide or an organolithium compound at a temperature of -70.degree. C. to 65.degree. C. Protected phosphine oxides so prepared are useful intermediates for the preparation of tertiary phosphine oxides and acylphosphine oxide photoinitiators.

Process for the preparation of protected phosphine oxides

3,5-Dihalogeno-1,2,6-thiadiazin-4-ones of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are chlorine, fluorine or bromine, in particular 3,5-dichloro-1,2,6-thiadiazin-4-one, are excellently suitable for use as biocides for the protection of industrial materials and for water systems, for example for wood, plastics, paints, oils, adhesives and industrial water circulation systems.

Biocides for protecting industrial materials and water systems

Arylphenyl ether derivatives of the formula ##STR1## wherein Az is 1H-(1,2,4-triazolyl) or is 1-imidazolyl optionally substituted by alkyl,

Arylphenyl ether derivatives, compositions containing these compounds

Compounds of formula ##STR1## wherein: R.sub.1 is phenyl, naphthyl, phenyl substituted from one to five times by R.sub.6, or naphthyl substituted from one to five times by R.sub.6 ; R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted at least once by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, phenyl, phenyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.1 -C.sub.3 alkyl, benzyl, or benzyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.1 -C.sub.3 alkyl; R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl or the radical CO-R.sub.7 ; R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by halogen and/or by methyl, C.sub.1 -C.sub.4 alkyl substituted at least once by halogen, hydroxy and/or by cyano, C.sub.2 -C.sub.5 alkynyl, C.sub.1 -C.sub.4 alkylthio or the radical CH.sub.2 XR.sub.8 ; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted at least once by halogen, hydroxy, cyano and/or by C.sub.1 -C.sub.3 alkoxy, R.sub.5 is also C.sub.3 -C.sub.5 alkenyl, halogen, hydroxy, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.3 -C.sub.6 cycloalkyl or C.sub.1 -C.sub.3 alkylthio; R.sub.6, independently of any other, is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl substituted by C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy, halogen, cyano, nitro, hydroxy or the radical S(O).sub.n -C.sub.1 -C.sub.4 alkyl; R.sub.7 is C.sub.1 -C.sub.6 alkyl, or C.sub.1 -C.sub.6 alkyl substituted at least once by halogen and/or by C.sub.1 -C.sub.3 alkoxy; R.sub.8 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted at least once by halogen, hydroxy, cyano and/or by C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub. 6 alkenyl, C.sub.3 -C.sub.6 alkynyl or C.sub.3 -C.sub.6 cycloalkyl; X is oxygen or sulfur; and n is 0, 1 or 2; including the acid addition compounds and the metal salt complexes thereof, have valuable microbicidal properties. The novel compounds can be used in plant protection for preventing attacks on cultivated plants by phytopathogenic microorganisms and for controlling those microorganisms.

Pesticidal 2-hydrazinopyramidine compounds

Novel 1-phenoxyphenyl-1-triazolylmethyl-carbinols of formula I ##STR1## in which R.sub.1 is fluorine, chlorine or bromine and R.sub.2 is fluorine, chlorine, bromine or methyl, and the phytophysiologically tolerable acid addition salts thereof have excellent microbicidal, in particular phytofungicidal, properties. They can be used for controlling and/or preventing infections caused by microorganisms in useful plants. The preparation of these compounds and compositions containing them is described.

1-phenoxyphenyl-1-triazolylmethyl-carbinol compound as microbicides

1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.4 alkyl and Z is O or NH, a and b denote the number of occupied positions in the respective 6-membered ring, and a is a number from 1 to 3 and b is a number from 0 to 3, the individual groups R.sub.1 being identical or different when the sum of a and b is greater than 1, X is O, S or NH, each of R.sub.2 and R.sub.3, independently of the other, is C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, halogen or by cyano, or is C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 alkenyl or the radical ##STR3## wherein n is 0 or 1, or R.sub.2 and R.sub.3 are also together a C.sub.4 -C.sub.7 alkylene chain that together with the nitrogen atom may form a heterocycle that is unsubstituted or mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, it being possible for one of the methylene groups in this chain to be replaced by O, S or NR.sub.7, and for R.sub.2 also to be hydrogen. The compounds of formula I have microbicidal activity and can be used advantageously for plant protection.

Substituted 1-aryl-2-napthoylamines and their use as microbicides

The described novel pyridine derivatives are those of the general formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3, or benzyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3,

Substituted 1,3-dioxolane compounds and their use as fungicides

The invention discloses novel N-(2-nitrophenyl)-2-aminopyrimidine derivatives of the general formula I ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, NO.sub.2 or CF.sub.3, with the proviso that only R.sub.1 or R.sub.2 can be NO.sub.2 ;

Pesticidal compositions

The invention discloses novel N-(2-nitrophenyl)-2-aminopyrimidine derivatives of the general formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently NO.sub.2 or CF.sub.3, with the proviso that only R.sub.1 or R.sub.2 can be NO.sub.2

N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use

There are described novel organotin compounds of the formula I ##STR1## wherein R.sub.1 is unsubstituted or substituted lower alkyl, lower alkenyl, cycloalkyl, furyl or tetrahydrofuryl;

Organotin compounds and pesticidal compositions

Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,

Microbicidal N-(tetrahydro-2-on-fur-3-yl)-N-substituted acetyl-anilines

A description is given of new compounds of the formula defined herein: ##STR1## which display valuable microbicidal properties. The compounds can be used for combatting microorganisms harmful to plants, especially phytopathogenic fungi. The compounds of formula I thus possess a curative, systemic, and preventive action very useful for practical requirements for the protection of cultivated plants, without causing these to suffer any undesirable side effects. In practice, the compounds can be used by themselves or in the form of pesticides.

1-[2-(4-Diphenyl)-1,3-dioxolan-2-yl-methyl]-1-H-triazoles

Microbicidal N-alkoxycarbonyl-alkyl-N-substituted acetyl-anilines and

There are described novel homoserine derivatives of the formula (I) ##STR1## which possess valuable microbicidal properties. In the formula: Ar is substituted phenyl or naphthyl; R.sub.1 is C.sub.2 -C.sub.6 alkyl optionally interrupted by oxygen or sulfur, 2-furyl, 2-tetrahydrofuryl, 1H-1,2,4-triazolylmethyl, 1-imidazolylmethyl, 1-pyrazolylmethyl, C.sub.2 -C.sub.4 alkenyl or cyclopropyl, each of which is optionally substituted by halogen; R.sub.2 is hydrogen or methyl; R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and B is halogen or an ester, thioester, sulfonic acid ester or sulfonic acid amide group. Additionally, where B is halogen, R.sub.1 may be halomethyl. The novel derivatives can be used for combating microorganisms harmful to plants, particularly for combating phytopathogenic fungi, and they have for practical requirements a very favorable curative and protective action for protecting cultivating plants, without the plants being impaired as a result of undesirable secondary effects. A notable feature is their stability to heat and to solar irradiation. They can be used in practice on their own or in the form of pesticidal compositions.

Growing community of inventors

Buckten, Switzerland

Peter Riebli