# US 9,040,457 B2 · Phenylamidines having a high fungicidal activity and use thereof

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- Number: US 9,040,457 B2
- Document ID: US9040457B2
- Status: Granted
- Kind: B2
- Application number: 13/818,622
- Filed: 2011-08-18
- Published: 2013-06-20
- Granted: 2015-05-26
- Earliest claimed: 2010-08-23
- Assignees: Isagro S.p.A.
- Applicants: Marilena Gusmeroli; Lucio Filippini; Franco Pellacini; Paolo Bravini; Alexia Elmini; Matteo Santino Vazzola; Christian Badaracco
- Inventors: Marilena Gusmeroli; Lucio Filippini; Franco Pellacini; Paolo Bravini; Alexia Elmini; Matteo Santino Vazzola; Christian Badaracco
- Web page: https://patentgrep.com/patent/US9040457B2

## CPC

- C07C 323/41: Y being a hydrogen or an acyclic carbon atom
- A01N 37/52: containing [IMAGE cpc-sch-A01N-0939.gif] groups, e.g. carboxylic acid amidines
- A01N 43/36: five-membered rings
- A01N 43/40: six-membered rings
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/84: six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- C07D 213/70: Sulfur atoms
- C07D 231/44: Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D 237/18: Sulfur atoms
- C07D 239/56: One oxygen atom and one sulfur atom
- C07D 241/18: Oxygen or sulfur atoms
- C07D 295/13: to an acyclic saturated chain
- C07D 295/195: Radicals derived from nitrogen analogues of carboxylic acids
- C07C 2601/02: with a three-membered ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

New phenylamidines are described, having general formula (I): and their use for the control of phytopathogenic fungi.

## Claims

### Claim 1

Phenylamidines having general formula (I):
wherein
R represents a phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group, wherein said phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group is substituted by at least a substituent selected from C1-C6 polyfluoroalkoxy containing at least one hydrogen atom, C1-C6 polyfluoroalkylthio containing at least one hydrogen atom, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, or C4-C8 halocycloalkylalkoxy; said phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl being optionally substituted by one or two further substituents, equal to or different from each other, selected from halogen atom, C1-C6 alkyl, or C1-C6 haloalkyl;
R1 represents C2-C6 alkyl;
R2 represents C1-C6 alkyl;
or R1 and R2, together with the N atom to which they are bound, form a heterocyclic ring containing from 4 to 7 atoms, optionally substituted by halogen atoms;
R3 and R4, equal to or different from each other, represent a hydrogen atom, a halogen atom, a C1-C6 alkyl, a C1-C6 alkoxy, a C1-C6 haloalkoxy, a CF3 group, a CF2H group, a CFH2 group, or a cyano group.

### Claim 2 (depends on 1)

The phenylamidines according to claim 1, wherein:
R represents a phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group, wherein said phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group is substituted by at least a substituent selected from difluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2,2,3,3,4,4,5,5-octa-fluoropentoxy, cyclopentoxy, cyclohexyloxy, cyclopropylmethoxy or cyclohexylmethoxy; said phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group being optionally substituted by one or two further substituents, equal to or different from each other, selected from a fluorine atom, a chlorine atom, methyl or trifluoromethyl;
R1 represents ethyl, n-propyl, or isopropyl;
R2 represents methyl; or R1 and R2, together with the N atom to which they are bound, represent a pyrrolidyl, piperidyl or morpholyl group;
R3 and R4 represent methyl.

### Claim 3 (depends on 1)

The phenylamidines according to claim 1, selected from compounds having general formula (I) wherein:
R represents a phenyl group substituted by at least a substituent selected from difluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2,2,3,3,4,4,5,5-octa-fluoropentoxy, cyclopentoxy, cyclohexyloxy, cyclopropylmethoxy or cyclohexylmethoxy; said phenyl group being optionally substituted by one or two further substituents, equal to or different from each other, selected from a fluorine atom, a chorine atom, methyl or trifluoromethyl;
R1 represents ethyl, n-propyl, or isopropyl;
R2 represents a methyl; or R1 and R2, together with the N atom to which they are bound, represent a pyrrolidyl, piperidyl or morpholylgroup;
R3 and R4 represent methyl.

### Claim 4 (depends on 1)

A fungicidal compositions comprising one or more compounds of formula (I), according to claim 1, in combination with a solvent and/or a solid or liquid diluent, and optionally a surfactant.

### Claim 5 (depends on 4)

The compositions according to claim 4, also comprising active principles compatible with the compounds having general formula (I), selected from fungicides other than the compounds having general formula (I), phytoregulators, antibiotics, herbicides, insecticides, fertilizers and/or mixtures thereof, antifreeze agents, or adhesion agents.

### Claim 6 (depends on 4)

The compositions according to claim 4, wherein the concentration of compounds having general formula (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, with respect to the total weight of the composition.

### Claim 7

A method for the control of phytopathogenic fungi of agricultural crops comprising applying an effective amount of a phenylamidine selected from general formula (I):
wherein:
R represents a phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group, wherein said phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl group is substituted by at least a substituent selected from C1-C6 polyfluoroalkoxy containing at least one hydrogen atom, C1-C6 polyfluoroalkylthio containing at least one hydrogen atom, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, or C4-C8 halocycloalkylalkoxy; said groups phenyl, pyridyl, pyrimidyl, pyrazyl or pyridazyl being optionally substituted by one or two further substituents, equal to or different from each other, selected from halogen atom, C1-C6 alkyl, or C1-C6 haloalkyl;
R1 represents C2-C6 alkyl;
R2 represents C1-C6 alkyl;
or R1 and R2, together with the N atom to which they are bound, form a heterocyclic ring containing from 4 to 7 atoms, optionally substituted by halogen atoms;
R3 and R4, equal to or different from each other, represent a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, a CF3 group, a CF2H group, a CFH2 group, or a cyano group to phytopathogenic fungi of agricultural crops.

### Claim 8 (depends on 2)

A method for the control of phytopathogenic fungi of agricultural crops comprising applying an effective amount of a compound according to claim 2, to phytopathogenic fungi of agricultural crops.

### Claim 9 (depends on 4)

A method for the control of phytopathogenic fungi of agricultural crops comprising applying an effective amount of a composition according to claim 4 to phytopathogenic fungi in agricultural crops.

### Claim 10 (depends on 7)

A method for the control of phytopathogenic fungi of agricultural crops comprising applying an effective amount of a compound according to claim 7 where said phytopathogenic fungi are selected from the group consisting of Basidiomycetes, Ascomycetes, Deuteromycetes or imperfect fungi, Oomycetes: Puccinia spp., Ustilago spp., Tilletia spp., Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerotinia spp., Septoria spp. (Mycosphaerella spp.), Venturia spp., Botrytis spp., Alternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, or Bremia lactucae.

### Claim 11 (depends on 7)

A method for the control of phytopathogenic fungi of agricultural crops comprising applying an effective amount of a compound to an agricultural crop according to claim 7, wherein the agricultural crop is selected from the group consisting of cereals, fruit trees, citrus trees, leguminous plants, horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, or cotton.

### Claim 12 (depends on 7)

A method for the control of phytopathogenic fungi comprising applying an effective amount of a compound Use according to claim 7 to Plasmopara viticola on vines; Phytophtora infestans and Botrytis Cinerea on tomatoes; Puccinia recondita, Erysiphe graminis, Helminthosporium teres, Septoria nodorum and Fusarium spp. on cereals; Phakopsora pachyrhizi on soybean; Uromyces Appendiculatus on beans; Venturia inaequalis on apple trees; or Sphaerotheca fuliginea on cucumbers.

### Claim 13 (depends on 1)

A method for the control of bacteria or phytopathogenic viruses of agricultural crops comprising applying an effective amount of a compound according to claim 1, for the control of bacteria and phytopathogenic viruses.

### Claim 14 (depends on 1)

A method for controlling phytopathogenic fungi in agricultural crops, which consists in applying effective dosages of a compound according to claim 1, in amounts ranging from 10 g to 5 kg per hectare of agricultural crop.

### Claim 15 (depends on 4)

The compositions according to claim 4, wherein the concentration of compounds having general formula (I) ranges from 5 to 50% by weight with respect to the total weight of the composition.