IP Library Granted Patent US 9,192,160
Granted Patent B2
US 9,192,160 · App. 13/995,853 · Granted Nov 24, 2015

Aminoindanes amides having a high fungicidal activity and their phytosanitary compositions

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,192,160
App. No.
13/995,853
Granted
Nov 24, 2015
Kind
B2
Abstract

New aminoindanes amides are described, having general formula (I) the relative phytosanitary compositions and their use for the control of phytopathogenic fungi.

Claims (39)

1. Aminoindane amides having structural formula (I) or isomers thereof:

wherein:

R 1 , R 2 and R 4 , equal to or different from each other, represent a C 1 -C 3 alkyl group;

R 3 represents a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group;

R 5 represents a halogen atom, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylthio group;

n represents an integer ranging from 1 to 3;

A represents the following heterocycle:

wherein the unconnected bond in said heterocycle represents a molecular bond to the carboxmide group of structure of formula (I);

R 6 is a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, an SH group, a C 1 -C 4 alkylthio group, a C 1 -C 4 haloalkylthio group.

2. The compounds according to claim 1 , characterized in that in formula (I), A represents A 1 , R 1 , R 2 , R 4 and R 6 are a methyl group, R 3 is a hydrogen atom, R 5 represents a halogen.

3. The compounds according to claim 1 , selected from the following compounds having general formula (I):

3-difluoromethyl-N-(7-fluoro-1,1,3-trimethyl-4-indanyl)-1-methyl-4-pyrazolecarboxamide;

3-difluoromethyl-1-methyl-N-(7-methoxy-1,1,3-trimethyl-4-indanyl)-4-pyrazolecarboxamide;

3-difluoromethyl-1-methyl-N-(7-trifluoromethoxy-1,1,3-trimethyl-4-indanyl)-4-pyrazolecarboxamide;

3-difluoromethyl-1-methyl-N-(7-methylthio-1,1,3-trimethyl-4-indanyl)-4-pyrazolecarboxamide;

3-difluoromethyl-N-(7-chloro-1,1,3-trimethyl-4-indanyl)-1-methyl-4-pyrazolecarboxamide.

4. The compounds according to claim 1 , characterized in that they are in the form of racemic mixtures, diastereoisomeric mixtures, partially separated mixtures, single optical isomers and/or single diastereoisomers.

5. Fungicidal compositions comprising one or more compounds having formula (I) according to claim 1 , a solvent and/or solid or liquid diluent and a surfactant.

6. The compositions according to claim 5 , 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, preferably from 5 to 50% by weight with respect to the total weight of the composition.

7. A method for the control of phytopathogenic fungi of agricultural crops which comprises applying to an agricultural crop an effective amount of an aminoindane amide having structural formula (I):

wherein:

R 1 , R 2 and R 4 , equal to or different from each other, represent a C 1 -C 3 alkyl group;

R 3 represents a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group;

R 5 represents a halogen atom, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylthio group;

n represents an integer ranging from 1 to 3;

A represents the following heterocycle:

wherein the unconnected bond in said heterocycle represents a molecular bond to the carboxamide group of structure of formula (I);

R 6 is a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, an SH group, a C 1 -C 4 alkylthio group, a C 1 -C 4 haloalkylthio group,

for the control of phytopathogenic fungi of agricultural crops.

8. A method for the control of phytopathogenic fungi of agricultural crops which comprises applying to an agricultural crop an effective amount of a compounds according to claim 2 .

9. A method for the control of phytopathogenic fungi of agricultural crops which comprises applying to agricultural crops an effective amount of a composition according to claim 5 .

10. The method of claim 7 , for the control of phytopathogenic fungi belonging to the group of Basidiomycetes, Ascomycetes, Deuteromycetes or fungi imperfecti, 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, and Bremia lactucae.

11. The method of claim 7 , wherein the agricultural crops are cereals, fruit trees, citrus fruits, legumes, horticultural crops, cucurbits, oleaginous plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton.

12. The method of claim 7 for the control of Plasmopara viticola on vines, Phytophtora infestans and Botrytis Cinerea on tomatoes, Puccinia recondita, Erisiphae graminis, Helminthosporium teres, Septoria nodorum and Fusarium spp. on cereals; Phakopsora pachyrhizi on soya; Uromyces appendiculatus on beans; Venturia inaequalis on apples, Sphaeroteca fuliginea on cucumbers.

13. A method for the control of phytopathogenic fungi of agricultural crops which comprises applying to an agricultural crop an effective amount of a compound according to claim 1 for the control of phytopathogenic bacteria or viruses.

14. A method for controlling phytopathogenic fungi in agricultural crops, which consists in applying effective doses of compounds according to claim 1 in amounts ranging from 10 g to 5 kg of compound having formula (I) per hectare of agricultural crop.

15. A method for the control of phytopathogenic fungi of agricultural crops which comprises applying to an agricultural crop an effective amount of a composition according to claim 5 for the control of phytopathogenic bacteria or viruses.

16. A method for controlling phytopathogenic fungi in agricultural crops, which consists in applying effective doses of fungicidal compositions according to claim 5 , in amounts ranging from 10 g to 5 kg of compound having formula (I) per hectare of agricultural crop.

Assignments (5)
CHANGE OF ADDRESS Recorded Sep 14, 2025
From: FMC IP TECHNOLOGY GMBH
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 072892/0066 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2024
From: FMC AGRO SINGAPORE PTE. LTD.
To: FMC IP TECHNOLOGY GMBH
Reel/Frame 067639/0738 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2023
From: FMC AGRICULTURAL PRODUCTS INTERNATIONAL AG
To: FMC AGRO SINGAPORE PTE. LTD.
Reel/Frame 062539/0825 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2022
From: STICHTING I-F PRODUCT COLLABORATION
To: FMC AGRICULTURAL PRODUCTS INTERNATIONAL AG
Reel/Frame 059436/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2013
From: VENTURINI, ISABELLA; VAZZOLA, MATTEO SANTINO; SINANI, ENTELA; PELLACINI, FRANCO; FILIPPINI, LUCIO
To: STICHTING I-F PRODUCT COLLABORATION
Reel/Frame 031177/0532 →