Ciba-geigy Corporation

Rudolf Wehrli

Laurenz Gsell

Peter Ackermann

Jozef Drabek

Saleem Farooq

Odd Kristiansen

Karl Hoegerle

Hanspeter Fischer

Rudolph C Thummel

Prop-1-ynyl-3-phenoxybenzyl-2,2-dimethyl-3-(2',2'-dihalovinyl)-cyclopropane -1-carboxylates of the formula ##STR1## in which X.sub.1 if fluorine, chlorine or bromine, and their use in combating pests.

Insecticidal

4-N,N-Dimethylcarbamoyloxy-6-aminopyrimidines, and salts thereof, of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group, R.sub.3 is halogen or C.sub.1 -C.sub.5 -alkyl, and R.sub.4 is C.sub.1 -C.sub.5 -alkyl, or R.sub.3 is hydrogen and R.sub.4 is C.sub.2 -C.sub.5 -alkyl. There are described a process for producing these pyrimidines, their use for combating pests, and also the intermediates of the formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group, R.sub.3 is halogen or C.sub.1 -C.sub.5 -alkyl, and R.sub.4 is C.sub.1 -C.sub.5 -alkyl, or R.sub.3 is hydrogen and R.sub.4 is C.sub.2 -C.sub.5 -alkyl.

4-N,N-Dimethylcarbamoyloxy-6-aminopyrimidines and salts thereof, and

2-Methyl-4-N,N-dimethylcarbamoyloxy-6-amino-pyrimidines, and salts thereof, of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.5 -alkenyl or C.sub.2 -C.sub.5 -alkynyl, or together they are a C.sub.2 -C.sub.5 -alkylene group; a process for producing these pyrimidines; and their use for combating pests.

2-Methyl-4-N,N-dimethylcarbamoyloxy-6-amino-pyrimidines and salts

The invention relates to cyclopropanecarboxylic acid esters of the formula ##STR1## wherein X.sub.1 is methyl or halogen, R.sub.1 is hydrogen, cyano, --CSNH.sub.2, allenyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl, and R.sub.2 is unsubstituted or substituted alkenyl or alkynyl. A process for obtaining these compounds and their use in pest control are also disclosed.

Cyclopropanecarboxylic acid esters and use thereof in pest control

The invention relates to .alpha.-isopropyl- and .alpha.-cyclopropylphenylacetates of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, allenyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl, R.sub.2 is unsubstituted or substituted alkenyl or alkynyl, R.sub.3 is isopropyl or cyclopropyl, and each of R.sub.4 and R.sub.5 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, or both together are the methylenedioxy radical. A process for the production of these compounds and their use in pest control are disclosed.

.alpha.-Isopropyl- and .alpha.-cyclopropylphenylacetates and use thereof

The invention relates to 3-phenoxybenzyl compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl and R.sub.2 is alkenyl or alkynyl, as intermediates for the production of biocides. The preparation of the 3-phenoxybenzaldehydes employed as intermediates is described. Novel 3-phenoxybenzaldehydes used as starting materials and the production thereof are also disclosed.

3-Phenoxybenzyl compounds

Cyclopropanecarboxylic acid esters of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, methyl, trifluoromethyl or methoxy, and X.sub.1 and X.sub.2 are each halogen. A process for producing the above compounds and their use in pest control, as well as .alpha.-haloethynyl-3-phenoxy-benzyl alcohols.

Dihalovinylcyclopropanecarboxylic acid esters and their use in pest

The invention describes cyclopropanecarboxylic acid .alpha.-allenyl-3-phenoxybenzyl esters of the formula ##STR1## wherein X.sub.1 is halogen and each of Y.sub.1 and Y.sub.2 is hydrogen or halogen, a process for the production of these compounds, and the use thereof for controlling a variety of pests of animals and plants. The intermediates of the formula ##STR2## wherein X is hydroxyl or halogen and each of Y.sub.1 and Y.sub.2 is hydrogen or halogen, are also described.

Pesticidal

.alpha.-Prop-1-ynyl-3-phenoxybenzyl alcohols of the formula ##STR1## wherein Y represents hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, cyano or dimethylamino, a process for their manufacture and their use as intermediates for the synthesis of compounds which are suitable for pest control, and which are especially suitable because of their low fish toxicity, for the control of rice pests e.g. Chilo suppressalis in rice paddies where fish are kept.

.alpha.-Prop-1-ynyl-3-phenoxybenzyl alcohols

Phenylacetates of the formula ##STR1## wherein R.sub.1 is isopropyl or cyclopropyl, R.sub.2 is hydrogen, cyano, ethynyl, prop-1-ynyl or --CSNH.sub.2, and X.sub.1 is hydrogen, methyl, fluorine or chlorine, a process for their production and method of use thereof in pest control.

Cyclopropanecarboxylic acid-.alpha.-haloethynyl-m-phenoxybenzyl esters of the formula ##STR1## wherein R.sub.1 is ##STR2## R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, and

Cyclopropanecarboxylic acid-.alpha.-haloethynyl-m-phenoxybenzyl esters

1-(Dicyano-trimethylsiloxy)methyl-2,2-dimethylcyclopropane derivatives of the formula ##STR1## wherein R.sub.1 is ##STR2## and X.sub.1 is halogen. A process for the production of these compounds and their use as intermediates for obtaining biocidal compounds is described.

Novel cyclopropane derivatives

Acetates of the formula ##STR1## wherein X.sub.1 represents hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, X.sub.2 represents hydrogen or halogen, and Y represents hydrogen, halogen or methyl, processes for their manufacture and a method of controlling pests which comprises the use of these compounds.

Novel esters

Triazolylcarbamates of the formula ##STR1## wherein R.sub.1 is hydrogen, chlorine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, processes for producing them, and their use for combating insect pests.

N-N-Dimethyl-1-(1'-methyl-2'-methoxyethyl)-1,2,4-triazolylcarbamates

.alpha.-Phenyl-.alpha.-cyclopropylacetates of the formula ##STR1## wherein X.sub.1 represents hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, X.sub.2 represents hydrogen, methyl or halogen, R.sub.1 represents hydrogen, cyano, vinyl or ethynyl, and Y represents fluorine or bromine, processes for their manufacture, and a method of controlling pests which comprises the use of these novel esters.

Growing community of inventors

Rheinfelden, Switzerland

Rudolf Wehrli