US2006135538A1PendingUtilityA1
7-(R)-aminotriazolopyrimidines, their preparation and their use for controlling phytopathogenic fungi
Est. expiryNov 13, 2020(expired)· nominal 20-yr term from priority
Inventors:Jordi BlascoKlaus DitrichHubert SauterOliver CullmannMarkus GewehrWassilios GrammenosBernd MullerThomas GroteAndreas GypserJoachim RheinheimerIngo RosePeter SchaferFrank SchieweckEberhard AmmermannSiegfried StrathmannGisela LorenzReinhard Stierl
C07D 487/04A01N 43/90
50
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Claims
Abstract
7-(R)-Aminotriazolopyrimidines of the formula I where the substituents and the index are as defined below: R 1 is hydrogen or methyl; R 2 is methyl; R 3 is C 2 -C 1 o-alkyl, C 1 -C 4 -alkoxymethyl, C 3 -C 1 o-cycloalkyl; R 4 is halogen, Cl-C 4 -alkyl, C 1 -C 4 -haloalkyl or Cl-C 4 -alkoxy; n is a number from 1 to 5; Y is halogen, cyano, Cl-C 4 -alkyl or C l -C 4 -alkoxy; where * is a center of chirality in the R configuration, processes for preparing these compounds, compositions comprising them and their use for controlling harmful fungi are described.
Claims
exact text as granted — not AI-modified1 . A compound of formula I
where
R 1 is hydrogen or methyl;
R 2 is methyl;
R 3 is C 2 -C 10 -alkyl; C 1 -C 4 -alkoxymethyl; C 3 -C 10 -cycloalkyl;
R 4 n is 2,6-dichloro. 2-chloro-6-fluoro or 2-chloro:
y is halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and
where * is a center of chirality in the R configuration, excluding the compounds sec-butyl-[5-chloro-6-(2-chloro-6-fluoro-phenyl)- [1,2,4]triazolo[1,5-a]pyrimidin-7-yI]-amine and [5-chloro-6-(2-chloro-6-fluoro- phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-yl]-( 1 ,2,2-trimethyl-propyl)-a mine.
2 . A compound of the formula I as claimed in claim 1 , where
R 1 is hydrogen; R 3 is C 2 -C 10 -alkyl or C 3 -C 10 -cycloalkyl; and Y is chlorine.
3 . A compound of the formula I as claimed in claim 2 , where
R 3 is tert-butyl or isopropyl.
4 . A compound of the formula I as claimed in claim 1 , where
(R 4 ) n , has the following meaning:
5 . A process for preparing the compounds I as claimed in claim 1 , which comprises reacting a 7-halotriazolopyrimidine of the formula II,
in which the substituents R 4 and Y and the index n are as defined in claim 1 , with a (R)-configured amine of the formula III
in which the substituents,R 1 ,R 2 and R 3 are as defined in claim 1 .
6 . A process as claimed in claim 5 , wherein (R)-3,3-dimethylbut-2-ylamine or (R)-3-methylbut-2-ylamine is used.
7 . A process as claimed in claim 5 , wherein a (R)-configured amine of the formula III is prepared by
i) enantioselectively acylating, in the presence of a hydrolase, a racemic amine III with an ester whose acid component carries a fluorine, nitrogen, oxygen or sulfur atom in the vicinity of the carbonyl carbon,
ii) separating the mixture of (S)-amine III and acylated (R)-amine III and
iii) subjecting the acylated (R)-amine III to an amide cleavage.
8 . A fungicidal composition, comprising solid and/or liquid carriers and a fungicidally effective amount of at least one compound of the formula I as claimed in claim 1 .
9 . A method for controlling phytopathogenic fungi which comprises treating the fungi or the materials, plants, seeds or the soil threatened by fungal attack with a fungicidally effective amount of at least one compound of the formula I
where
R 1 is hydrogen or methyl;
R 2 is methyl;
R 3 is C 2 -C 10 -alkyl; C 1 -C 4 -alkoxymethyl; C 3 -C, 0 -cycloalkyl;
R 4 n is 2,6-dichloro, 2-chloro-6-fluoro or 2-chloro;
y is halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
where * is a center of chirality in the R configuration.
10 . The method of claim 9 , where R 4 n is 2,6-dichloro or 2- chloro-6-fluoro.
11 . The method of claim 9 , where the compound of formula I has the formula IA
where R 1 is hydrogen, R 3 is CH 2 CH 3 and R 4 n is 2-chloro.
12 . The method of claim 9 , where the compound of formula I has the formula IA
where R 1 is hydrogen, R 3 is CH(CH 3 ) 2 and R 4 n is 2-chloro.
13 . The method of claim 9 , where the compound of formula I has the formula IA
where R 1 is hydrogen, R 3 is C(CH 3 ) 3 and R 4 n is 2-chloro.
14 . The compound of claim 1 , having the formula IA
where R 1 is hydrogen, R 3 is CH 2 CH 3 and R 4 n is 2-chloro.
15 . The compound of claim 1 , having the formula IA
where R 1 is hydrogen, R 3 is CH(CH 3 ) 2 and R 4 n is 2-chloro.
16 . The compound of claim 1 , having the formula IA
where R 1 is hydrogen, R 3 is C(CH 3 ) 3 and R 4 n is 2-chloro.Cited by (0)
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