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AssigneeNovartis Animal Health US, Inc.
InventorsMartin Eberle, André Jeanguenat, Werner Zambach, Arthur Steiger, Saleem Farooq
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The invention relates to compounds of the general formula wherein R1 is unsubstituted or mono- to penta-substituted aryl, whereby the substituents are selected from the group consisting for instance of OH, Halogen, CN, C1-C6-alkyl, optionally substituted C3-C8-cycloalkyl and optionally substituted C3-C8-cycloalkenyl; A is for instance a single bond, C1-C12-alkylene or O; X1 and X2, independently of one another, are R10; X3 is H or R10; R10 is for instance halogen, CN, NO2, C1-C6-alkyl, C3-C8-cycloalkyl or C1-C6-haloalkyl; R21 and R22, independently of one another are for instance H, halogen, CN, NO2, OH, SH, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl or C3-C8-cycloalkyl-C1-C6-alkyl; R23 and R24, independently of one another, are for instance H, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl or C3-C8-halocycloalkyl; m is 1, 2, 3 or 4; and n is 0, 1 or 2; as well as the physiologically acceptable addition compounds, a method of producing these compounds and the usage of these compounds, pesticide compositions whose active ingredient is chosen from these compounds, each in free form or in agrochemically employable salt form, and a method of producing and using these compositions. The active ingredients, in free form or in agrochemically employable salt form, have advantageous pesticidal properties. The are especially suitable for the control of pests in agriculture and in storage, as well as in the care of domestic animals.
A compound of formula
Dependencies are inferred from the claim text.
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Having three or more double bonds between ring members or between ring members and non-ring members: with only hydrogen atoms, hydrocarbon or…
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,3-Diazines; Hydrogenated 1,3-diazines
Antiparasitic agents: ectoparasiticides, e.g. scabicides
Having three or more double bonds between ring members or between ring members and non-ring members: with hetero atoms or with carbon atoms having…
Term ended 2 May 2020 (estimated)
The present invention relates to new pyrimidine derivatives of formula
wherein
R1 is unsubstituted or mono- to penta-substituted aryl, whereby the substituents are selected from the group consisting of OH, Halogen, CN, C1-C6-alkyl, optionally substituted C3-C8-cycloalkyl, optionally substituted C3-C8-cycloalkenyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C3-C8-cycloalkoxy, C1-C6-haloalkoxy, C3-C8-halocycloalkoxy, C1-C6-alkylthio, C3-C8-cycloalkylthio, C1-C6-haloalkylthio, C3-C8-halocycloalkylthio, C1-C6-alkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-halocycloalkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-halocycloalkylsulfonyl, optionally substituted C2-C8-alkenyl, optionally substituted C2-C8-alkinyl, C1-C6-alkylcarbonyl, —C(═NOR6)—C1-C6-Alkyl; R7; unsubstituted or mono- to penta-substituted phenyl; unsubstituted or mono- to penta-substituted heteroaryl, whereby the substituents are respectively selected from the group consisting of OH, halogen, CN, NO2, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C3-C8-cycloalkoxy, C1-C6-haloalkoxy, C3-C8-halocycloalkoxy, C1-C6-alkylthio, C3-C8cycloalkylthio, C1-C6-haloalkylthio, C3-C8-halocycloalkylthio, C3-C8-alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-halocycloalkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-halocycloalkylsulfonyl, C2-C8-alkenyl, C2-C8-alkinyl, C1-C6-alkylcarbonyl, —C(═NOR6)—C1-C6-Alkyl and R7; unsubstituted or mono- to penta-substituted phenoxy; unsubstituted or mono- to penta-substituted phenylthio; unsubstituted or mono- to penta-substituted phenylamino and unsubstituted or mono- to penta-substituted —N(phenyl)(C1-C6-alkyl), whereby the substituents are respectively selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C3-C8-cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C3-C8-cycloalkoxy, C1-C6-alkylthio, C3-C8cycloalkythio, C1-C6-haloalkylthio and C3-C8-halocycloalkylthio;
17.4 g of tert.-butyl hypochlorite are added dropwise to a solution of 26.1 g of 2,6-difluorobenzaldehyde oxime in 200 ml of methylene chloride in such a way that the temperature can be maintained at 20° C. After one hour, the reaction mixture is slowly added dropwise to 100 ml of a saturated methanolic ammonia solution. After a further hour, it is poured onto water, concentrated under vacuum, and the crystalline precipitate obtained is filtered and dried.
The hydroxamic acid amide thus obtained in 220 ml of hydrochloric-acid-containing ethanol is hydrogenated at 3 bars and at 60° C. over 9 g of Raney nickel. After filtering, concentrating under vacuum and recrystallising from ether, the title compound is obtained with a melting point of >250° C.
32 ml of phosphorus oxychloride are added dropwise at 10-15° C., with good cooling and intensive stirring, to 45 ml of dimethylformamide. Subsequently, 25 g of 4-bromophenylacetic acid are added in portions at −10° C., and the reaction mixture is stirred for 1 hour at room temperature, then for 2 hours at 60° C. and finally for 5 hours at 80° C. The mixture is then carefully hydrolysed with 20 ml of water at 0° C., and the product is precipitated by adding 35 ml of 70% perchloric acid. After filtering and recrystallising from acetone/ether, the title compound is obtained in the form of colourless crystals with a melting point of 160° C.