Fungicide pyrazole carboxamides derivatives

Inventors: Guenter Bartels (Burgwedel, DE); Angela Becker (Dusseldorf, DE); Juergen Benting (Leichlingen, DE); Christoph-Andreas Braun (Dusseldorf, DE); Peter Dahmen (Neuss, DE); Philippe Desbordes (Lyons, FR); Christophe Dubost (Charbonnieres-les-Bains, FR); Stephanie Gary (Champagne-au-Mont-d'Or, FR); Ulrich Gorgens (Ratingen, DE); Hiroyuki Hadano (Shimotsuke, JP); Benoit Hartmann (Sainte-Foy-les-Lyon, FR); Thomas Knobloch (Chatillon d'Azergues, FR); Marc Kosten (Weyhe, DE); Norbert Lui (Odenthal, DE); Ruth Meissner (Leverkusen, DE); Sergiy Pazenok (Solingen, DE); Rachel Rama (Lyons, FR); Arnd Voerste (Cologne, DE); Ulrike Wachendorff-Neumann (Neuwied, DE)

Assignee: BAYER INTELLECTUAL PROPERTY GMBH

C07D231/16 A01N43/56 A01N55/00 C07D401/12 C07F7/0812

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Quick Facts

Patent No.: US 9,695,126
App. No.: 15/188,164
Granted: Jul 4, 2017
Kind: B2

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Abstract

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CR 5 or N, T represents S or O, X1 and X2 represent a chlorine or a fluorine atom, and Z1 represents a substituted or non-substituted cyclopropyl; Their process of preparation, their use as fungicide, and/or anti-mycotoxin active agents, and/or insecticide, and/or nematicide, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

Claims (39)

1. A method for the preparation of a compound of the formula

according to the following scheme:

wherein:

Y is selected from the group consisting of CR 5 and nitrogen;

T is selected from the group consisting of sulfur and oxygen;

X 1 and X 2 are independently selected from the group consisting of a chlorine atom and a fluorine atom;

Z 1 is selected from the group consisting of a non substituted cyclopropyl and a cyclopropyl substituted by up to 2 atoms or groups independently selected from the group consisting of halogen; cyano; C 1 -C 8 -alkyl; and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different;

Z 2 and Z 3 , which can be the same or different, represent a hydrogen atom; substituted or non substituted C 1 -C 8 -alkyl; substituted or non substituted C 2 -C 8 -alkenyl; substituted or non substituted C 2 -C 8 -alkynyl; cyano; isonitrile; nitro; a halogen atom; substituted or non substituted C 1 -C 8 -alkoxy; substituted or non substituted C 2 -C 8 -alkenyloxy; substituted or non substituted C 2 -C 8 -alkynyloxy; substituted or non substituted C 3 -C 7 -cycloalkyl; substituted or non substituted C 1 -C 8 -alkylsulfanyl; substituted or non substituted C 1 -C 8 -alkylsulfonyl; substituted or non substituted C 1 -C 8 -alkylsulfinyl; amino; substituted or non substituted C 1 -C 8 -alkylamino; substituted or non substituted di-C 1 -C 8 -alkylamino; substituted or non substituted C 1 -C 8 -alkoxycarbonyl; substituted or non substituted C 1 -C 8 -alkylcarbamoyl; substituted or non substituted di-C 1 -C 8 -alkylcarbamoyl; or substituted or non substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; or

Z 3 and R 1 together with the consecutive carbon atoms to which they are linked form a substituted or non substituted 5-, 6- or 7-membered, partly saturated, carbo- or heterocycle comprising up to 3 heteroatoms and Z 2 is as herein described; or

Z 2 and Z 3 together with the carbon atom to which they are linked form a substituted or non substituted C 3 -C 7 cycloalkyl;

R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen; halogen; nitro; cyano; isonitrile; hydroxyl; sulfanyl; amino; pentafluoro-λ 6 -sulfanyl; substituted or non substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -alkylamino; substituted or non substituted di-C 1 -C 8 -alkylamino; substituted or non substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; substituted or non substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 2 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; substituted or non substituted C 3 -C 7 -cycloalkyl-C 2 -C 8 -alkenyl; substituted or non substituted C 3 -C 7 -cycloalkyl-C 2 -C 8 -alkynyl; substituted or non substituted C 3 -C 7 -cycloalkyl-C 3 -C 7 -cycloalkyl; substituted or non substituted C 1 -C 8 -alkyl-C 3 -C 7 -cycloalkyl; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C 1 -C 8 -alkyl; substituted or non substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -alkylcarbamoyl; substituted or non substituted di-C 1 -C 8 -alkylcarbamoyl; N-(substituted or non substituted C 1 -C 8 -alkyloxy)carbamoyl; substituted or non substituted C 1 -C 8 -alkoxycarbamoyl; N-(substituted or non substituted C 1 -C 8 -alkyl)-(substituted or non substituted C 1 -C 8 -alkoxy)-carbamoyl; substituted or non substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 alkylaminocarbonyl; di-substituted or non substituted C 1 -C 8 -alkylaminocarbonyl; substituted or non substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -lkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -alkylaminocarbonyloxy; substituted or non substituted di-C 1 -C 8 alkylaminocarbonyloxy; substituted or non substituted C 1 -C 8 -alkyloxycarbonyloxy; substituted or non substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 1 -C 8 -alkoxyimino; (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non substituted (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; (C 1 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; a (benzyloxyimino)-C 1 -C 8 -alkyl; tri(substituted or non substituted C 1 -C 8 -alkyl)silyl; tri(substituted or non substituted C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl; benzyloxy which can be substituted by up to 5 groups Q; benzylsulfanyl which can be substituted by up to 5 groups Q; benzylamino which can be substituted by up to 5 groups Q; aryl which can be substituted by up to 7 groups Q; aryloxy which can be substituted by up to 7 groups Q; arylamino which can be substituted by up to 7 groups Q; arylsulfanyl which can be substituted by up to 7 groups Q; aryl-C 1 -C 8 -alkyl which can be substituted by up to 7 groups Q; aryl-C 2 -C 8 -alkenyl which can be substituted by up to 7 groups Q; aryl-C 2 -C 8 -alkynyl which can be substituted by up to 7 groups Q; pyridinyl which can be substituted by up to 4 groups Q; pyridinyloxy which can be substituted by up to 4 groups Q; and aryl-C 3 -C 7 -cycloalkyl which can be substituted by up to 7 groups Q; or

Two vicinal substituents R together with the consecutive carbon atoms to which they are linked form a substituted or non substituted 5- or 6-membered, saturated, carbo- or heterocycle comprising up to 3 heteroatoms and the other substituents R are as herein-described; or

R 1 and Z 3 together with the consecutive carbon atoms to which they are linked form a substituted or non substituted 5-, 6- or 7-membered, partly saturated, carbo- or heterocycle comprising up to 3 heteroatoms, and R 2 to R 5 are as herein-described; and

each Q is independently selected from the group consisting of halogen; cyano; nitro; C 1 -C 8 -alkyl; C 1 -C 8 alkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; and tri(C 1 -C 8 )alkylsilyl or tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;

with the proviso that when Y is nitrogen , and T is oxygen, and Z 1 is a cyclopropyl group, and R 1 is a chlorine atom, and R 3 is a trifluoromethyl group, and R 2 and R 4 are hydrogen, then a least one of the substituents Z 2 or Z 3 is not a hydrogen atom.

2. The method of claim 1 wherein wherein Y is CR 5 .

3. The method of claim 1 wherein Y is nitrogen.

4. The method of claim 1 wherein T is oxygen.

5. The method of claim 1 wherein X 1 is a fluorine atom.

6. The method of claim 1 wherein X 2 is a fluorine atom.

7. The method of claim 1 wherein Z 1 is a non substituted cyclopropyl.

8. The method of claim 1 wherein Z 2 and Z 3 are independently selected from the group consisting of hydrogen atom and methyl.

9. The method of claim 8 wherein Z 2 is hydrogen.

10. The method of claim 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen; halogen; substituted or non substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; and substituted or non substituted C 1 -C 8 alkylsulfanyl.

11. The method of claim 1 wherein R 1 is selected from the group consisting of halogen; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; and C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.

12. The method of claim 1 wherein R 1 and R 5 are independently selected from the group consisting of halogen; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; and C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.

13. The method of claim 1 wherein the compound of formula (IIb) is