Substituted imidazole and (1,2,4)triazole compounds as fungicides

Patent metadata

Field	Value
Publication number	US-2016002179-A1
Application number	US-201314759498-A
Country	US
Kind code	A1
Filing date	Dec 18, 2013
Priority date	Jan 8, 2013
Publication date	Jan 7, 2016
Grant date	—

Abstract

The present invention relates to compounds of the formula I

wherein the variables are as defined in the claims and description, their preparation and the uses of compounds I.

First claim

1 - 14 . (canceled)

15 : A compound of the formula I

wherein
A and D have the meanings:
A is CH; and D is H, halogen or SR D , wherein
R D is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or CN;
or
A is N; and D is halogen or SR D , wherein
R D is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or CN;

R 1 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
R 2 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
wherein the aliphatic moieties of R 1 and/or R 2 may carry one, two, three or up to the maximum possible number of identical or different groups R 12a which independently of one another are selected from:
R 12a halogen, OH, CN, nitro, C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and C 1 -C 4 -halogenalkoxy;
wherein the cycloalkyl and/or phenyl moieties of R 1 and/or R 2 may carry one, two, three, four, five or up to the maximum number of identical or different groups R 12b which independently of one another are selected from:
R 12b halogen, OH, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and C 1 -C 4 -halogenalkoxy;

n is 0, 1, 2, 3 or 4;
R 3 is independently selected from halogen, CN, NO 2 , OH, SH, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, NH 2 , NH(C 1 -C 4 -alkyl), N(C 1 -C 4 -alkyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , S(O) p (C 1 -C 4 -alkyl), C(═O)(C 1 -C 4 -alkyl), C(═O)(OH), C(═O)(O—C 1 -C 4 -alkyl), C(═O)(NH(C 1 -C 4 -alkyl)), C(═O)(N(C 1 -C 4 -alkyl) 2 ), C(═O)(NH(C 3 -C 6 -cycloalkyl)) and C(═O)—(N(C 3 -C 6 -cycloalkyl) 2 ; wherein each of R 3 is unsubstituted or further substituted by one, two, three or four R 3a ; wherein
R 3a is independently selected from halogen, CN, NO 2 , OH, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; and wherein
p is 0, 1 or 2;

m is 0, 1, 2, 3, 4 or 5;
R 4 is independently selected from the substituents as defined for R 3 ; wherein said R 4 are unsubstituted or further substituted by one, two, three or four R 4a , wherein each R 4a is independently selected from the substituents as defined for R 3a ;
and the N-oxides and the agriculturally acceptable salts thereof.

16 : The compound of claim 15 , wherein A is N.

17 : The compound of claim 15 , wherein A is CH.

18 : The compound of claim 15 , wherein D is SR D .

19 : The compound of claim 15 , wherein D is halogen.

20 : The compound of claim 17 , wherein D is H.

21 : The compound of claim 20 , wherein R 12a is selected from halogen, OH, CN, nitro, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, n+m is 1, 2, 3, 4, 5, 6, 7, 8 or 9 and for n=0 and m=1, R 4 is not 4-Cl, 4-F or 4-Br, and for n=1 with R 3 =2-Cl and m=1, R 4 is not 4-Cl.

22 : The compound of claim 21 , wherein n is 1, 2, 3 or 4 and m is 1, 2, 3, 4 or 5 with the said proviso.

23 : The compound I of claim 15 , wherein D is SH, A is N, R 2 is H, R 1 is CH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl or 2-CF 3 ; the compounds I wherein D is SH, A is N, R 2 is H, R 1 is CH(CH 3 ) 2 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl or 2-CF 3 ; the compounds I wherein D is SH, A is N, R 2 is H, R 1 is cyclopropyl, (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl or 2-CF 3 ; the compound I wherein D is SH, A is N, R 2 is H, R 1 is C═CCH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl; and the compound I wherein D is SH, A is N, R 2 is CH 3 , R 1 is CH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-CF 3 .

24 : A composition comprising one compound of formula I, as defined in claim 15 , an N-oxide or an agriculturally acceptable salt thereof.

25 : The composition according to claim 24 , comprising additionally a further active substance.

26 : A method for combating harmful fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in claim 15 , or with a composition, as defined in claim 24 .

27 : Seed, coated with at least one compound of the formula I, as defined in claim 15 , and/or an agriculturally acceptable salt thereof or with a composition, as defined in claim 24 , in an amount of from 0.1 to 10 kg per 100 kg of seed.

28 : The method of claim 15 , wherein, in the compound of formula (I), A is N.

29 : The method of claim 15 , wherein, in the compound of formula (I), A is CH.

30 : The method of claim 15 , wherein, in the compound of formula (I), D is SR D .

31 : The method of claim 15 , wherein, in the compound of formula (I), D is halogen.

32 : The method of claim 29 , wherein, in the compound of formula (I), D is H.

33 : The method of claim 32 , wherein, in the compound of formula (I), R 12a is selected from halogen, OH, CN, nitro, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, n+m is 1, 2, 3, 4, 5, 6, 7, 8 or 9 and for n=0 and m=1, R 4 is not 4-Cl, 4-F or 4-Br, and for n=1 with R 3 =2-Cl and m=1, R 4 is not 4-Cl.

34 : The method of claim 33 , wherein, in the compound of formula (I), n is 1, 2, 3 or 4 and m is 1, 2, 3, 4 or 5 with the said proviso.

35 : The method of claim 15 , wherein, in the compound of formula (I), D is SH, A is N, R 2 is H, R 1 is CH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl or 2-CF 3 ; the compounds I wherein D is SH, A is N, R 2 is H, R 1 is CH(CH 3 ) 2 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl or 2-CF 3 ; the compounds I wherein D is SH, A is N, R 2 is H, R 1 is cyclopropyl, (R 4 ) m is 4-Cl and (R 3 ) n is 2-C 1 or 2-CF 3 ; the compound I wherein D is SH, A is N, R 2 is H, R 1 is C═CCH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-Cl; and the compound I wherein D is SH, A is N, R 2 is CH 3 , R 1 is CH 3 , (R 4 ) m is 4-Cl and (R 3 ) n is 2-CF 3 .

Assignees

• Basf Se

Inventors

• Grammenos Wassilios
• Craig Ian Robert
• Boudet Nadege
• Mueller Bernd
• Dietz Jochen
• Lauterwasser Erica May Wilson
• Lohmann Jan Klaas
• Grote Thomas
• Haden Egon
• Escribano Cuesta Ana

Classifications

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D233/60 Primary

  with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms · CPC title

• C07D249/12 Primary

  Oxygen or sulfur atoms · CPC title

• C07D233/84

  Sulfur atoms · CPC title

• C07D233/68

  Halogen atoms · CPC title