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AssigneeCiba-Geigy Corporation
InventorsManfred Boger, Jozef Drabek, Gunter Mattern, Walter Traber
Estimating the term…
Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each methyl or chlorine, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is methoxy, ethoxy, C.sub.1 -C.sub.4 -alkylthio or phenyl and X is oxygen or sulphur have valuable pesticidal in particular acaricidal properties.
A compound of the formula I ##STR10## wherein R.sub.1 and R.sub.2 are each independently methyl or chlorine, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is methoxy, ethoxy, C.sub.1 -C.sub.4 -alkylthio or phenyl and X is oxygen or sulphur.
Dependencies are inferred from the claim text.
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No related US applications are recorded in the indexed filing history.
No references of this kind are recorded.
Having phosphorus-to-nitrogen bonds: containing heterocyclic radicals
Five-membered rings: having the nitrogen atoms in positions 1 and 3
Preservation of bodies of humans or animals or plants or parts thereof
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen
Term ended 22 Oct 1999 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention relates to novel 1-phosphorylated 2-(phenoxy-alkyl)-2-imidazoline derivatives which are effective against pests, a process for their manufacture, pesticidal compositions which contain these derivatives as active component, and a method of controlling pests which comprises the use of the novel compounds.
2-(Phenoxyalkyl)-2-imidazolines having pesticidal, especially ectoparasiticidal, action are known (cf. for example South African patent application No. 78/2449, Japanese published patent specification No. 76/106739 and German Offenlegungsschrift No. 2 756 639). The present invention provides novel compounds of this type which also are effective against pests, especially against representatives of the order Acarina, and which are particularly suitable for practical use because of their advantageous biological properties.
The 1-phosphorylated 2-(phenoxyalkyl)-2-imidazoline derivatives of the present invention have the formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently chlorine or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is methoxy, ethoxy, C.sub.1 -C.sub.4 alkylthio or phenyl, and X is oxygen or sulfur.
The invention is illustrated in more detail by the following Examples.
6 g of triethylamine are added at 0.degree. C. to a solution of 11.6 g of 2-[1-(2,3-dimethylphenoxy)-propyl]-2-imidazoline in 100 ml of toluene. With continuous stirring, 8.6 g of diethyl chlorophosphate are then added slowly dropwise at 0.degree. to 10.degree. C. The resultant suspension is stirred for a further 2 hours at room temperature, diluted with a small amount of water and the toluene phase is washed with a small amount of water. The toluene solution is dried and concentrated and the residue is dried in a high vacuum, affording 1-(diethoxyphosphynyl)-2-[1-(2,3-dimethylphenoxy)-propyl]-2-imidazoline of the formula ##STR5## in the form of a clear yellow oil with a refraction of n.sub.D.sup.20 =1.5092. The following compounds of the formula I ##STR6## can be obtained in analogous manner:
______________________________________ Com- Physical pound R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 X data ______________________________________ 2 CH.sub.3 CH.sub.3 H CH.sub.3 CH.sub.3 O O m.p. 147-149.degree. C. 3 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 C.sub.2 H.sub.5 O O n.sub.D.sup.20 :1.5126 4 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 C.sub.2 H.sub.5 S O n.sub.D.sup.20 :1.5527 5 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 ##STR7## S n.sub.D.sup.20 :1.5960 6 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S O n.sub.D.sup.20 1.5431 7 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S S n.sub.D.sup.20 :1.5152 8 CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5421 9 CH.sub.3 CH.sub. 3 H C.sub.2 H.sub.5 (i)C.sub.4 H.sub.9 S O 10 CH.sub.3 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S O 11 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 O O n.sub.D.sup.20 :1.5231 12 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 S O n.sub.D.sup.20 :1.5399 13 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 ##STR8## S n.sub.D.sup.20 :1.5821 14 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S O n.sub.D.sup.20 1.5341 15 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S S n.sub.D.sup.20 :1.5609 16 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5314 17 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 (i)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5306 18 Cl Cl C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 O O 19 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 O 20 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 S O 21 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 ##STR9## S 22 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S O 23 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 (n)C.sub.3 H.sub.7 S S 24 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O 25 Cl Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 (i)C.sub.4 H.sub.9 S O 26 Cl CH.sub.3 (n)C.sub.4 H.sub.9 C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5235 27 Cl CH.sub.3 (n)C.sub.3 H.sub.7 C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5258 28 Cl CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 (s)C.sub.4 H.sub.9 S O n.sub.D.sup.20 :1.5380 ______________________________________