# US 8,772,266 B2 · Fungicide pyrazole carboxamides derivates

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- Number: US 8,772,266 B2
- Document ID: US8772266B2
- Status: Granted
- Kind: B2
- Application number: 13/319,614
- Filed: 2010-05-12
- Published: 2012-03-15
- Granted: 2014-07-08
- Earliest claimed: 2009-05-15
- Assignees: Bayer CropScience AG
- Applicants: Guenter Bartels; Angela Becker; Jurgen Benting; Christoph-Andreas Braun; Peter Dahmen; Philippe Desbordes; Christophe Dubost; Stephanie Gary; Ulrich Gorgens; Hiroyuki Hadano; Benoit Hartmann; Thomas Knobloch; Marc Kosten; Norbert Lui; Ruth Meissner; Sergiy Pazenok; Rachel Rama; Arnd Voerste; Ulrike Wachendorff-Neumann
- Inventors: Guenter Bartels; Angela Becker; Jurgen Benting; Christoph-Andreas Braun; Peter Dahmen; Philippe Desbordes; Christophe Dubost; Stephanie Gary; Ulrich Gorgens; Hiroyuki Hadano; Benoit Hartmann; Thomas Knobloch; Marc Kosten; Norbert Lui; Ruth Meissner; Sergiy Pazenok; Rachel Rama; Arnd Voerste; Ulrike Wachendorff-Neumann
- Web page: https://patentgrep.com/patent/US8772266B2

## CPC

- C07D 231/16: Halogen atoms or nitro radicals
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07F 7/0812: {comprising a heterocyclic ring}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention relates to pyrazole carboxamides derivatives of formula (1) wherein Y represents CR5 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

### Claim 1

A compound of formula (I)
wherein
Y is selected from the group consisting of CR5 and N;
T is selected from the group consisting of S and O;
X1 and X2 are independently selected from the group consisting of chlorine and fluorine;
Z1 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; C1-C8-alkyl; and C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
Z2 and Z3 are independently selected from the group consisting of hydrogen; substituted or non substituted C1-C8-alkyl; substituted or non substituted C2-C8-alkenyl; substituted or non substituted C2-C8-alkynyl; cyano; isonitrile; nitro; halogen; substituted or non substituted C1-C8-alkoxy; substituted or non substituted C2-C8-alkenyloxy; substituted or non substituted C2-C8-alkynyloxy; substituted or non substituted C3-C7-cycloalkyl; substituted or non substituted C1-C8-alkylsulfanyl; substituted or non substituted C1-C8-alkylsulfonyl; substituted or non substituted C1-C8-alkylsulfinyl; amino; substituted or non substituted C1-C8-alkylamino; substituted or non substituted di-C1-C8-alkylamino; substituted or non substituted C1-C8-alkoxycarbonyl; substituted or non substituted C1-C8-alkylcarbamoyl; substituted or non substituted di-C1-C8-alkylcarbamoyl; and substituted or non substituted N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl; or
Z3 and R1 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 hetero-cycle comprising up to 3 heteroatoms and Z2 is as herein described; or
Z2 and Z3 together with the carbon atom to which they are linked form a substituted or non substituted C3-C7 cycloalkyl;
R1, R2, R3, R4 and R5 are independently selected from the group consisting of hydrogen halogen; nitro; cyano; isonitrile; hydroxyl; sulfanyl; amino; pentafluoro-λ6-sulfanyl; substituted or non substituted C1-C8-alkyl; C1-C8-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylamino; substituted or non substituted di-C1-C8-alkylamino; substituted or non substituted C1-C8-alkoxy; C1-C8-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; C1-C8-alkoxy-C1-C8-alkyl; substituted or non substituted C1-C8-alkylsulfanyl; C1-C8-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C2-C8-alkenyl; C2-C8-halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C2-C8-alkynyl; C2-C8-halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C2-C8-alkenyloxy; C2-C8-halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C2-C8-alkynyloxy; C2-C8-halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C3-C7-cycloalkyl; C3-C7-halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C3-C7-cycloalkyl-C1-C8-alkyl; substituted or non substituted C3-C7-cycloalkyl-C2-C8-alkenyl; substituted or non substituted C3-C7-cycloalkyl-C2-C8-alkynyl; substituted or non substituted C3-C7-cycloalkyl-C3-C7-cycloalkyl; substituted or non substituted C1-C8 alkyl-C3-C7-cycloalkyl; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C1-C8-alkyl; substituted or non substituted C1-C8-alkylcarbonyl; C1-C8-halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylcarbamoyl; substituted or non substituted di-C1-C8-alkylcarbamoyl; N-(substituted or non substituted C1-C8 alkyloxy)carbamoyl; substituted or non substituted C1-C8-alkoxycarbamoyl; N-(substituted or non substituted C1-C8-alkyl)-(substituted or non substituted C1-C8-alkoxy)-carbamoyl; substituted or non substituted C1-C8-alkoxycarbonyl; C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylaminocarbonyl; di-substituted or non substituted C1-C8-alkylaminocarbonyl; substituted or non substituted C1-C8-alkylcarbonyloxy; C1-C8-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylcarbonylamino; C1-C8-halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylaminocarbonyloxy; substituted or non substituted di-C1-C8-alkylaminocarbonyloxy; substituted or non substituted C1-C8-alkyloxycarbonyloxy; substituted or non substituted C1-C8-alkylsulfinyl; C1-C8-halogenoalkylsulfinyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkylsulfonyl; C1-C8-halogenoalkylsulfonyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C1-C8-alkoxyimino; (C1-C8-alkoxyimino)-C1-C8-alkyl; substituted or non substituted (C1-C8-alkenyloxyimino)-C1-C8-alkyl; (C1-C8-alkynyloxyimino)-C1-C8-alkyl; a (benzyloxyimino)-C1-C8-alkyl; tri(substituted or non substituted C1-C8-alkyl)silyl; tri(substituted or non substituted C1-C8-alkyl)silyl-C1-C8-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-C1-C8 alkyl which can be substituted by up to 7 groups Q; aryl-C2-C8-alkenyl which can be substituted by up to 7 groups Q; aryl-C2-C8-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-C3-C7-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 hetero-cycle comprising up to 3 heteroatoms and the other substituents R are as herein-described; or
R1 and Z3 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 hetero-cycle comprising up to 3 heteroatoms, and R2 to R5 are as herein-described;
Each Q is independently selected from the group consisting of halogen; cyano; nitro; C1-C8-alkyl; C1-C8-alkoxy; C1-C8-alkylsulfanyl; C1-C8-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C1-C8-halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different; tri(C1-C8)alkylsilyl and tri(C1-C8)alkylsilyl-C1-C8-alkyl;
with the proviso that when Y is N, and T is O, and Z1 is a cyclopropyl group, and R1 is chlorine, and R3 is a trifluoromethyl group, and R2 and R4 are both hydrogen, then at least one of the substituents Z2 or Z3 is not hydrogen;
as well as salts, N-oxides, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein Y is CR5.

### Claim 3 (depends on 1)

The compound of claim 1 wherein Y is N.

### Claim 4 (depends on 1)

The compound to of claim 1 wherein T is O.

### Claim 5 (depends on 1)

The compound of claim 1 wherein X1 is fluorine.

### Claim 6 (depends on 1)

The compound of claim 1 wherein X2 is fluorine.

### Claim 7 (depends on 1)

The compound of claim 1 wherein Z1 is a non substituted cyclopropyl.

### Claim 8 (depends on 1)

The compound of claim 1 wherein Z2 and Z3 are independently selected from the group consisting of hydrogen and methyl.

### Claim 9 (depends on 1)

The compound of claim 1 wherein Z2 is hydrogen and Z3 is selected from the group consisting of hydrogen and methyl.

### Claim 10 (depends on 1)

The compound of claim 1 wherein R1, R2, R3, R4 and R5 are independently selected from the group consisting of hydrogen; halogen; substituted or non substituted C1-C8-alkyl; C1-C8-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non substituted C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl; and substituted or non substituted C1-C8-alkylsulfanyl.

### Claim 11 (depends on 1)

The compound of claim 1 wherein the substituent R1 is selected from the group consisting of halogen; C1-C8-alkyl; C1-C8-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl and C1-C8-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.

### Claim 12 (depends on 1)

The compound of claim 1 wherein the substitutents R1 and R5 are independently selected from the group consisting of halogen; C1-C8-alkyl; C1-C8-halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; C3-C7-cycloalkyl; tri(C1-C8-alkyl)silyl and C1-C8-halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different.

### Claim 13 (depends on 1)

A composition comprising, as an active ingredient, an effective amount of the compound of claim 1 and an agriculturally acceptable support, carrier or filler.

### Claim 14 (depends on 1)

A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the compound of claim 1 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.

### Claim 15 (depends on 1)

The compound of claim 1 used for controlling phytopathogenic fungi of crops or/and for the reduction of mycotoxins in plants and part of plants and/or as insecticide, and/or as nematicide.

### Claim 16 (depends on 13)

A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the composition of claim 13 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.

### Claim 17 (depends on 13)

The composition of claim 13 used for controlling phytopathogenic fungi of crops or/and for the reduction of mycotoxins in plants and part of plants and/or as insecticide, and/or as nematicide.

### Claim 18 (depends on 1)

The compound of claim 1 wherein said compound is N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

### Claim 19 (depends on 14)

The method of claim 14 wherein the compound is N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.