O,O'-Dialkyl-4,6-diphosphorylated pyrimidines and compositions and methods for combating arthropods containing them

O,O'-Dialkyl-4,6-diphosphorylated pyrimidines of the formula ##STR1## in which R and R.sup.2 each independently is alkyl, PA1 R.sup.1 and R.sup.3 each independently is alkyl, alkoxy, alkylthio, alkylamino or phenyl, PA1 R.sup.4 is hydrogen, alkyl, alkoxy, alkylthio or dialkylamino, PA1 R.sup.5 is hydrogen, halogen or alkyl, and PA1 X and Y each independently is oxygen or sulfur, with the proviso that at least one of the radicals, R, R.sup.1, R.sup.2 and R.sup.3 must be different from the others or that X must be different from Y, which possess arthropodicidal and nematicidal properties.

The present invention relates and and has for its objects the provision of 
particular new O,O'-dialkyl-4,6-diphosphorylated pyrimidines which possess 
arthropodicidal and nematicidal properties, active compositions in the 
form of mixtures of such compounds with solid and liquid dispersible 
carrier vehicles, and methods for producing such compounds and for using 
such compounds in a new way especially for combating pests, e.g., insects, 
acarids and nematodes, with other and further objects becoming apparent 
from a study of the within specification and accompanying examples. 
It is known from U.S. Pat. No. 2,754,243, German Published DAS Nos. 
1,170,401 and 1,197,878 and published Netherlands patent application No. 
6,713,142 that monophosphorylated pyrimidines, for example 
O,O-diethyl-O-[2-methylthio-(Compound A) and 
2-isopropyl-6-methyl-pyrimidin-(4)yl]-thionophosphoric acid ester 
(Compound B), and bis-(thionophosphoric acid ester)-diphenylsulfides and 
-di-sulfides, for example O,O,O',O'-tetraethyl-O,O'-thio-(Compound C) and 
-dithio-di-p-phenylene-thionophosphoric acid ester (Compound D), possess 
insecticidal and acaricidal properties. 
The present invention now provides, as new compounds, the diphosphorylated 
pyrimidines of the general formula 
##STR2## 
in which R and R.sup.2 each independently is alkyl, 
R.sup.1 and R.sup.3 each independently is alkyl, alkoxy, alkylthio, 
alkylamino or phenyl, 
R.sup.4 is hydrogen, alkyl, alkoxy, alkylthio or dialkylamino, 
R.sup.5 is hydrogen, halogen or alkyl, and 
X and Y each independently is oxygen or sulfur, with the proviso that at 
least one of the radicals, R, R.sup.1, R.sup.2 and R.sup.3 must be 
different from the others or that X must be different from Y, 
Preferably, R and R.sup.2, which may be identical or different, each 
represent straight-chain or branched alkyl with 1 to 4 carbon atoms, 
R.sup.1 and R.sup.3, which may be identical or different, each represent 
straight-chain or branched alkyl, alkoxy, alkylthio or monoalkylamino with 
in each case 1 to 4 carbon atoms or phenyl, R.sup.4 represents hydrogen, 
straight-chain or branched alkyl with 1 to 4 carbon atoms or 
straight-chain or branched alkoxy, alkylthio or dialkylamino each with 1 
to 3 carbon atoms per alkyl radical, R.sup.5 represents hydrogen, 
chlorine, bromine or straight-chain or branched alkyl with 1 to 3 carbon 
atoms and X and Y each represent sulfur. 
Surprisingly, the diphosphorylated pyrimidines according to the invention 
exhibit a better insecticidal and acaricidal action than the corresponding 
previously known compounds of similar structure and of the same type of 
action. The products of the present invention thus represent a genuine 
enrichment of the art. 
The present invention also provides a process for the preparation of a 
diphosphorylated pyrimidine of the formula (I) in which an 
O-[6-hydroxypyrimidin(4)yl]-(thiono)(thiol)-phosphoric(phosphonic) acid 
ester or ester-amide of the general formula 
##STR3## 
in which R, R.sup.1, R.sup.4, R.sup.5 and X have the meanings mentioned 
above, is reacted, either in the form of an alkali metal salt, alkaline 
earth metal salt or ammonium salt thereof or as such in the presence of an 
acid acceptor, if appropriate in the presence of a solvent or diluent, 
with a (thiono)(thiol)phosphoric(phosphonic) acid ester halide or 
ester-amide halide of the general formula 
##STR4## 
in which R.sup.2, R.sup.3 and Y have the abovementioned meanings and 
Hal represents halogen, preferably chlorine. 
If, for example, 
O-[2-ethylthio-5-chloro-6-hydroxypyrimidin(4)yl]-O-ethyl-N-iso-propyl-thio 
nophosphoric acid diester-amide and O-iso-propyl-ethanephosphonic acid 
ester chloride are used as starting materials, the course of the reaction 
can be represented by the following equation: 
##STR5## 
The O-[6-hydroxy-pyrimidin(4)yl]-(thiono)(thiol)phosphoric (phosphonic) 
acid esters and ester-amides (II) to be used as starting materials can be 
prepared in accordance with generally customary processes described in the 
literature, for example by reacting 4,6-dihydroxypyrimidines with 
(thiono)(thiol)phosphoric(phosphonic) acid ester halides or ester-amide 
halides, if appropriate in the presence of acid acceptors and, if 
appropriate, in the presence of a solvent, in accordance with the 
following equation: 
##STR6## 
wherein R, R.sup.1, R.sup.4, R.sup.5 and X have the abovementioned 
meanings and 
Hal.sup.1 represents halogen, preferably chlorine. 
The following may be mentioned as individual examples: 
O-[6-hydroxy-pyrimidin(4)yl]-, O-[6-hydroxy-2-methylpyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-pyrimidin(4)yl], 
O-[6-hydroxy-2-iso-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-butylpyrimidin(4)yl]-, 
O-[6-hydroxy-2-sec.-butyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-butyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methoxy-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethoxy-pyrimidin(4) yl]-, 
O-[6-hydroxy-2-n-propoxy-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-propoxy-pyrimidin(4)yl]-, 
6-[6-hydroxy-2-methylthio-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthiopyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propylthio-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-propylthio-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-diethylamino-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-di-n-propylaminopyrimidin(4)yl]-, 
O-[6-hydroxy-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-5-bromo-pyrimidin(4)yl]-, O-[ 
6-hydroxy-5-methyl-pyrimidin(4)yl]-, O-[6-hydroxy-5-ethyl-pyrimidin 
(4)yl]-, O-[6-hydroxy-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-5-iso-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methyl-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethyl-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-propyl-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methoxy-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethoxy-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methylthio-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthio-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-diethylamino-5-chloro-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methyl-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethyl-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-isopropyl-5-bromo-pyrimidin(4)yl-, 
O-[6-hydroxy-2-methoxy-5-bromo-pyrimidin(4)yl]-, O-[6-hydroxy-2-ethoxy-5 
-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methylthio-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthio-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-diethylamino-5-bromo-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methyl-5-methyl-pyrimidin(4)yl-, 
O-[6-hydroxy-2-ethyl-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-isopropyl-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methoxy-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethoxy-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methylthio-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthio-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-diethylamino-5-methyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methyl-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethyl-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-propyl-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methoxy-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethoxy-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methylthio-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthio-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-diethylamino-5-ethyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methyl-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethyl-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-n-propyl-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-iso-propyl-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methoxy-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethoxy-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-methylthio-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-ethylthio-5-n-propyl-pyrimidin(4)yl]-, 
O-[6-hydroxy-2-dimethylamino-5-n-propyl-pyrimidin(4)yl]-, O-[ 
6-hydroxy-2-diethylamino-5-n-propyl-pyrimidin(4)yl]-O,O-dimethyl-, 
-O,O-diethyl-, -O,O-di-n-propyl-, -O,O-di-iso-propyl-, -O,O-di-n-butyl-, 
-O,O-di-isobutyl-, -O,O-di-sec.-butyl-, -O-methyl-O-ethyl-, 
-O-methyl-O-n-propyl-, -O-methyl-O-iso-propyl-, -O-methyl-O-n-butyl-, 
-O-methyl-O-iso-butyl-, -O-methyl-O-sec.-butyl-, -O-methyl-O-tert.-butyl-, 
-O-ethyl-O-n-propyl-, -O-ethyl-O-iso-propyl-, -O-ethyl-O-n-butyl-, 
-O-ethyl-O-sec.-butyl-, -O-ethyl-O-iso-butyl-, -O-n-propyl-O-butyl- and 
-O-iso-propyl-O-butyl-thionophosphoric acid ester, as well as 
-O,S-dimethyl-, -O,S-diethyl-, -O,S-di-n-propyl-, -O,S-di-iso-propyl-, 
-O,S-di-n-butyl-, -O,S-di-iso-butyl-, -O,S-di-tert.-butyl-, 
-O-ethyl-S-n-propyl-, -O-ethyl-S-iso-propyl-, -O-ethyl-S-n-butyl-, 
-O-ethyl-S-sec.-butyl-, -O-n-propyl-S-ethyl-, -O-n-propyl-S-iso-propyl-, 
-O-n-butyl-S-n-propyl- and -O-sec.-butyl-S-ethyl-thionothiolphosphoric 
acid ester and -O-methyl-, -O-ethyl-, -O-n-propyl-, -O-iso-propyl-, 
-O-n-butyl-, -O-iso-butyl-, -O-sec.-butyl- and -O-tert.-butyl-methane-, 
-ethane-, -n-propane-, -iso-propane-, -n-butane-, -iso-butane-, 
-tert.-butane-, -sec.-butane- and -benzene-thionophosphonic acid diester, 
and -O-methyl-N-methyl-, -O-methyl-N-ethyl-, -O-methyl-N-n-propyl-, 
-O-ethyl-N-methyl-, -O-ethyl-N-ethyl-, -O-ethyl-N-n-propyl-, 
-O-ethyl-N-iso-propyl-, -O-n-propyl-N-methyl-, -O-n-propyl-N-ethyl, 
-O-n-propyl-N-n-propyl, -O-n-propyl-N-iso-propyl-, 
-O-iso-propyl-N-methyl-, -O-iso-propyl-N-ethyl-, -O-iso-propyl-N-n-butyl- 
and -O-n-butyl-N-n-butyl-thionophosphoric acid diester amide. 
The (thiono)(thiol)phosphoric(phosphonic) acid ester halides and 
ester-amide halides (III) which are also to be used as starting materials 
are known and can be prepared in accordance with processes described in 
the literature. The following may be mentioned as individual examples of 
these compounds: O,O-dimethyl-, O,O-diethyl-, O,O-di-n-propyl-, 
O,O-di-iso-propyl-, O,O-di-n-butyl-, O,O-di-iso-butyl-, O,O-disec.-butyl-, 
O-methyl-O-ethyl-, O-methyl-O-n-propyl-, O-methyl-O-iso-propyl-, 
O-methyl-O-n-butyl-, O-methyl-O-iso-butyl-, O-methyl-O-sec.-butyl-, 
O-methyl-O-tert.-butyl-, O-ethyl-O-n-propyl-, O-ethyl-O-iso-propyl-, 
O-ethyl-O-n-butyl-, O-ethyl-O-sec.-butyl-, O-ethyl-O-iso-butyl-, 
O-n-propyl-O-butyl- and O-iso-propyl-O-butyl-phosphoric acid diester 
halides and the corresponding thiono analogues; O,S-dimethyl-, 
O,S-diethyl-, O,S-di-n-propyl-, O,S-di-iso-propyl-, O,S-di-n-butyl-, 
O,S-di-iso-butyl-, O,S-di-tert.-butyl-, O-ethyl-S-n-propyl-, 
O-ethyl-S-iso-propyl-, O-ethyl-S-n-butyl-, O-ethyl-S-sec.-butyl-, 
O-n-propyl-S-ethyl-, O-n-propyl-S-iso-propyl-, O-n-butyl-S-n-propyl- and 
O-sec.-butyl-S-ethyl-thiolphosphoric acid diester halides and the 
corresponding thiono analogues; O-methyl-, O-ethyl-, O-n-propyl-, 
O-iso-propyl-, O-n-butyl-, O-iso-butyl-, O-sec.-butyl- and 
O-tert.-butyl-methane-, ethane-, n-propane-, iso-propane, n-butane-, 
isobutane-, tert.-butane-, sec.-butane- and -benzene-phosphonic acid ester 
halides and the corresponding thiono analogues; and O-methyl-N-methyl-, 
O-methyl-N-ethyl-, O-methyl-N-n-propyl-, O-methyl-N-iso-propyl-, 
O-methyl-N-n-butyl-, O-methyl-N-sec.-butyl-, O-methyl-N-iso-butyl-, 
O-ethyl-N-methyl-, O-ethyl-N-ethyl-, O-ethyl-N-n-propyl-, 
O-ethyl-N-iso-propyl-, O-ethyl-N-n-butyl-, O-ethyl-N-isobutyl-, 
O-ethyl-N-sec.-butyl-, O-n-propyl-N-methyl-, O-n-propyl-N-ethyl-, 
O-n-propyl-N-n-propyl-, O-n-propyl-N-iso-propyl-, O-n-propyl-N-n-butyl-, 
O-n-propyl-N-iso-butyl-, O-n-propyl-N-sec.-butyl-, O-iso-propyl-N-methyl-, 
O-iso-propyl-N-ethyl-, O-iso-propyl-N-n-propyl-, 
O-iso-propyl-N-iso-propyl-, O-iso-propyl-N-n-butyl-, 
O-iso-propyl-N-iso-butyl- O-iso-propyl-N-sec.-butyl-, O-n-butyl-N-methyl-, 
O-n-butyl-N-ethyl-, O-n-butyl-N-n-propyl-, O-n-butyl-N-iso-propyl-, 
O-n-butyl-N-n-butyl-, O-iso-butyl-N-ethyl-, O-iso-butyl-N-iso-propyl- and 
O-iso-butyl-N-n-propyl-phosphoric acid ester-amide halides and the 
corresponding thiono analogues. 
The process for the preparation of the compounds according to the invention 
is preferably carried out in the presence of a suitable solvent or 
diluent. Virtually all inert organic solvents can be used for this 
purpose, especially aliphatic and aromatic, optionally chlorinated 
hydrocarbons, such as benzene, toluene, xylene, benzine, methylene 
chloride, chloroform, carbon tetrachloride and chlorobenzene; ethers, for 
example diethyl ether, dibutyl ether and dioxane; ketones, for example 
acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl 
ketone; and nitriles, such as acetonitrile and propionitrile. 
All customary acid-binding agents can be used as acid acceptors. Alkali 
metal carbonates and alkali metal alcoholates, such as sodium carbonate 
and potassium carbonate, sodium methylate and ethylate and potassium 
methylate and ethylate, have proved particularly suitable, as have 
aliphatic, aromatic or heterocyclic amines, for example triethylamine, 
trimethylamine, dimethylaniline, dimethylbenzylamine and pyridine. 
The reaction temperature can be varied within a fairly wide range. In 
general, the reaction is carried out at between 0.degree. and 120.degree. 
C., preferably at 35.degree. to 60.degree. C. 
In general, the reaction is allowed to take place under normal pressure. 
To carry out the process, the starting components are preferably employed 
in equimolar amounts. An excess of one or other component produces no 
essential advantages. The reactants are in general brought together in one 
of the stated solvents and are stirred for one or more hours, in most 
cases at an elevated temperature, to complete the reaction. Thereafter, an 
organic solvent, for example toluene, is added and the organic phase is 
worked up in the usual manner by washing, drying and distilling off the 
solvent. 
The new compounds are obtained in the form of oils which in most cases 
cannot be distilled without decomposition but are freed from the last 
volatile constituents by so-called "slight distillation," that is to say 
be prolonged heating under reduced pressure to moderately elevated 
temperatures, and are purified in this manner. They are characterized by 
the refractive index. 
As already mentioned, the diphosphorylated pyrimidines according to the 
invention are distinguished by an excellent insecticidal and acaricidal 
activity. They are active against plant pests, pests harmful to health and 
pests of stored products. They combine a low phytotoxicity with a good 
action against both sucking and biting insects and mites. 
For this reason, the compounds according to the invention can be employed 
successfully as pesticides in plant protection and in the hygiene field 
and the field of protection of stored products. 
The active compounds are well tolerated by plants, have a favorable level 
of toxicity to warm-blooded animals, and can be used for combating 
arthropod pests, especially insects and arachnids, and nematode pests 
which are encountered in agriculture, in forestry, in the protection of 
stored products and of materials, and in the hygiene field. They are 
active against normally sensitive and resistant species and against all or 
some stages of development. The above-mentioned pests include: from the 
class of the Isopoda, for example Oniscus asellus, Armadillidium vulgare 
and Porcellio scaber; from the class of the Diplopoda, for example 
Blaniulus guttulatus; from the class of the Chilopoda, for example 
Geophilus carpophagus and Scutigera spec.; from the class of the Symphyla, 
for example Scutigerella immaculata; from the order of the Thysanura, for 
example Lepisma saccharina; from the order of to Collembola, for example 
Onychiurus armatus; from the order of the Orthoptera, for example Blatta 
orientalis, Periplaneta americana, Leucophaea maderae, Blattella 
germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria 
migratorioides, Melanoplus differentialis and Schistocerca gregaria; from 
the order of the Dermaptera, for example Forficula auricularia; from the 
order of the Isoptera, for example Reticulitermes spp.; from the order of 
the Anoplura, for example Phylloxera vastatrix, Pemphigus spp., Pediculus 
humanus corporis, Haematopinus spp. and Linognathus spp.; from the order 
of the Mallophaga, for example Trihodectes spp. and Damalinea spp.; from 
the order of the Thysanoptera, for example Hercinothrips femoralis and 
Thrips tabaci; from the order of the Heteroptera, for example Eurygaster 
spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius 
prolixus and Triatoma spp.; from the order of the Homoptera, for example 
Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis 
gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis 
pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus 
spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis 
bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, 
Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, 
Aspidiotus hederae, Pseudococcus ssp. and Psylla spp., from the order of 
the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, 
Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, 
Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, 
Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis 
spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma 
exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera 
spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., 
Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia 
podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, 
Homona magnanima and Tortrix viridana; from the order of the Coleoptera, 
for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, 
Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, 
Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., 
Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., 
Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus 
sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera 
postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., 
Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus holoeucus, Gibbium 
psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus 
spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra 
zealandica; from the order of the Hymenoptera, for example Diprion spp., 
Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.; from 
the order of the Diptera, for example Aedes spp., Anopheles spp., Culex 
spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora 
erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., 
Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma 
spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia 
spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula 
paludosa; from the order of the Siphonaptera, for example Xenopsylla 
cheopis and Ceratophyllus spp.; from the class of the Arachnida, for 
example Scorpio maurus and Latrodectus mactans; from the order of the 
Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., 
Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus 
spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp, 
Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia 
praetiosa, Panonychus spp. and Tetranychus spp.. 
The plant-parasitic nematodes include Pratylenchus spp., Radopholus 
similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., 
Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp. and 
Trichodorus spp.. 
When used against hygiene pests and pests of stored products, the active 
compounds are distinguished by an excellent residual activity on wood and 
clay as well as a good stability to alkali on limed substrates. 
The active compounds according to the instant invention can be utilized, if 
desired, in the form of the usual formulations or compositions with 
conventional inert (i.e., plant compatible or herbicidally inert) 
pesticide diluents or extenders, i.e., diluents, carriers or extenders of 
the type usable in conventional pesticide formulations or compositions, 
e.g., conventional pesticide dispersible carrier vehicles such as gases, 
solutions, emulsions, wettable powders, suspensions, powders, dusting 
agents, foams, pastes, soluble powders, granules, aerosols, 
suspension-emulsion concentrates, seed-treatment powders, natural and 
synthetic materials impregnated with active compound, very fine capsules 
in polymeric substances and in coating compositions, for use on seed, and 
formulations used with burning equipment, such as fumigating cartridges, 
fumigating cans, fumigating coils and the like, as well as ULV cold mist 
and warm mist formulations. 
These are prepared in known manner, for instance by extending the active 
compounds with conventional pesticide dispersible liquid diluent carriers 
and/or dispersible solid carriers optionally with the use of carrier 
vehicle assistants, e.g., conventional pesticide surface-active agents, 
including emulsifying agents and/or dispersing agents, whereby, for 
example, in the case where water is used as diluent, organic solvents may 
be added as auxiliary solvents. The following may be chiefly considered 
for use as conventional carrier vehicles for this purpose: aerosol 
propellants which are gaseous at normal temperatures and pressures, such 
as halogenated hydrocarbons as well as butane, propane, nitrogen and 
carbon dioxide; inert dispersible liquid diluent carriers, including inert 
organic solvents, such as aromatic hydrocarbons (e.g., benzene, toluene, 
xylene, alkyl naphthalenes, etc.), halogenated, especially chlorinated, 
aromatic hydrocarbons (e.g., chlorobenzenes, etc.), cycloalkanes, (e.g., 
cyclohexane, etc.), paraffins (e.g., petroleum or mineral oil fractions), 
chlorinated aliphatic hydrocarbons (e.g., methylene chloride, 
dichlorodifluoromethane, trichlorofluoromethane, chloroethylenes, etc.), 
alcohols (e.g., methanol, ethanol, propanol, butanol, glycol, etc.) as 
well as ethers and esters thereof (e.g., glycol monomethyl ether, etc.), 
amines (e.g., ethanolamine, etc.), amides (e.g., dimethyl formamide, 
etc.), sulfoxides (e.g., dimethyl sulfoxide, etc.), acetonitrile, ketones 
(e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, 
cyclohexanone, etc.), and/or water; as solid carriers, ground natural 
minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, 
montmorillonite or diatomaceous earth, and ground synthetic minerals, such 
as highly-dispersed silicic acid, alumina and silicates; as solid carriers 
for granules; crushed and fractionated natural rocks such as calcite, 
marble, pumice, sepiolite and dolomite, as well as synthetic granules of 
inorganic and organic meals, and granules of organic material such as 
sawdust, coconut shells, maize cobs and tobacco stalks; whereas the 
following may be chiefly considered for use as conventional carrier 
vehicle assistants, e.g., surface-active agents, for this purpose: 
emulsifying agents, such as non-ionic and/or anionic emulsifying agents 
(e.g., polyethylene oxides esters of fatty acids, polyethylene oxide 
ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl 
sulfonates, albumin hydrolyzates, etc., and especially alkyl 
arylpolyglycol ethers, magnesium stearate, sodium oleate, etc.); and/or 
dispersing agents, such as lignin, sulfite waste liquors, methyl 
cellulose, etc. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, can be used in the formulations. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
Such active compounds may be employed alone or in the form of mixtures with 
one another and/or with such solid and/or liquid dispersible carrier 
vehicles and/or with other known compatible active agents, especially 
plant protection agents, such as other insecticides and acaricides, or 
fungicides, bactericides, rodenticides, herbicides, fertilizers, 
growth-regulating agents, etc., if desired, or in the form of particular 
dosage preparations for specific application made therefrom, such as 
solutions, emulsions, suspensions, powders, pastes, and granules which are 
thus ready for use. 
As concerns commercially marketed preparations, these generally contemplate 
carrier composition mixtures in which the active compound is present in an 
amount substantially between about 0.1-95% by weight, and preferably 
0.5-90% by weight, of the mixture, whereas carrier composition mixtures 
suitable for direct application or field application generally contemplate 
those in which the active compound is present in an amount substantially 
between about 0.0000001-100, preferably 0.01-10%, by weight of the 
mixture. Thus, the present invention contemplates overall compositions 
which comprise mixtures of a conventional dispersible carrier such as (1) 
a dispersible inert finely divided carrier solid, and/or (2) a dispersible 
carrier liquid such as an inert organic solvent and/or water, preferably 
including a surface-active effective amount of a carrier vehicle 
assistant, e.g. a surface-active agent, such as an emulsifying agent 
and/or a dispersing agent, and an amount of the active compound which is 
effective for the purpose in question and which is generally between about 
0.0001-95%, and preferably 0.01-95%, by weight of the mixture. 
The active compounds can also be used in accordance with the well known 
ultra-low-volume process with good success, i.e. by applying such compound 
if normally a liquid, or by applying a liquid composition containing the 
same, via very effective atomizing equipment, in finely divided form, 
e.g., average particle diameter of from 50-100 microns, or even less, 
i.e., mist form, for example by airplane crop spraying techniques. Only up 
to at most about a few liters/hectare are needed, and often amounts only 
up to about 15 to 1000 g/hectare, preferably 40 to 600 g/hectare, are 
sufficient. In this process it is possible to use highly concentrated 
liquid compositions with said liquid carrier vehicles containing from 
about 20 to about 95% by weight of the active compound or even the 100% 
active substance alone, e.g., about 20-100% by weight of the active 
compound. 
When used against nematodes, the preparations are generally applied to an 
area of agriculture in amounts of 1 to 100 kg of active compound per 
hectare, and are then incorporated into the soil. 
Furthermore, the present invention contemplates methods of selectively 
killing, combating or controlling pests, e.g., arthropods and nematodes, 
which comprises applying to at least one of correspondingly (a) such 
arthropods, (b) such nematodes and (c) the corresponding habitat thereof, 
i.e., the locus to be protected, e.g., to a growing crop, to an area where 
a crop is to be grown or to a domestic animal, a correspondingly combative 
or toxic amount, i.e., an arthropodicidally or nematicidally effective 
amount, of the particular active compound of the invention alone or 
together with a carrier vehicle as noted above. The instant formulations 
or compositions are applied in the usual manner, for instance by spraying, 
atomizing, vaporizing, scattering, dusting, watering, squirting, 
sprinkling, pouring, fumigating, and the like. 
It will be realized, of course, that the concentration of the particular 
active compound utilized in admixture with the carrier vehicle will depend 
upon the intended application. Therefore, in special cases it is possible 
to go above or below the aforementioned concentration ranges.