FIELD OF THE INVENTION:
5 The present invention relates to novel picolinamide compounds which are useful in combating
phytopathogenic fungi, and to a process for preparing these picolinamide compounds. The present
invention also relates to a composition, a combination comprising these novel picolinamide
compounds, and a method for combating phytopathogenic fungi using the same.
BACKGROUND OF THE INVENTION:
10 Picolinamide compounds are described as fungicidal agents in WO2016109288, WO2016109289,
WO2016109300, WO2016109301, WO2016109302, WO2016109303, WO200114339, and
WO2016122802. The picolinamide compounds reported in the above cited literature have
disadvantages in certain aspects, such as that they exhibit a narrow spectrum of efficacy or that they
do not have satisfactory fungicidal activity, particularly at low application rates.
15 Therefore, the need remains for the development of new fungicidal compounds, including such that
are belonging to the class of the above cited picolinamides, so as to provide compounds being
effective against a broader spectrum of fungi, having lower toxicity, higher selectivity, being used at
lower dosage rate to reduce or avoid unfavorable environmental or toxicological effects whilst still
allowing effective and long-lasting control.
20 Therefore, it is an objective of the present invention to provide compounds having an
improved/enhanced activity and/or a broader efficacy spectrum against phytopathogenic fungi.
This objective is achieved by using a compound of formula (I) of the present invention for combating
phytopathogenic fungi.
SUMMARY OF THE INVENTION:
25 The present invention relates to a compound of formula (I),
Formula (I)
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wherein, R
1
, R
1a, R2
, W, R
3
, R
4
, R5
, R
6
, R7
, R8
and A are as defined in the detailed description. The
present invention also relates to a process for preparing the compound of formula (I).
The compounds of formula (I) have been found to be advantageous over the compounds reported in
the literature in either of improved fungicidal activity, broader spectrum of biological efficacy, lower
5 application rates, more favourable biological, environmental properties or enhanced plant
compatibility.
The present invention further relates to an agrochemical composition comprising a compound of
formula (I) or a compound of formula (I) in combination with a further pesticidally active substance
for controlling and/or preventing plant diseases, particularly caused by phytopathogenic fungi.
10 The present invention still further relates to a method for controlling or preventing infestation of
useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a
compound of formula (I), a composition or a combination thereof, is applied to the plants, to parts
thereof or the locus thereof.
DETAILED DESCRIPTION OF THE INVENTION:
15 DEFINITIONS:
The definitions provided herein for the terminologies used in the present disclosure are for illustrative
purpose only and in no manner limit the scope of the present invention disclosed in the present
disclosure.
As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”,
20 “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a
non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition,
mixture, process or method that comprises a list of elements is not necessarily limited to only those
elements but may include other elements not expressly listed or inherent to such composition,
mixture, process or method.
25 The transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the
claim, such would close the claim to the inclusion of materials other than those recited except for
impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the
body of a claim, rather than immediately following the preamble, it limits only the element set forth in
that clause; other elements are not excluded from the claim as a whole.
30 The transitional phrase “consisting essentially of” is used to define a composition or method that
includes materials, steps, features, components or elements, in addition to those literally disclosed,
provided that these additional materials, steps, features, components or elements do not materially
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affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially
of” occupies a middle ground between “comprising” and “consisting of”.
Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive
“or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present)
5 and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B
are true (or present).
Also, the indefinite articles “a” and “an” preceding an element or component of the present invention
are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or
component. Therefore “a” or “an” should be read to include one or at least one, and the singular word
10 form of the element or component also includes the plural unless the number is obviously meant to be
singular.
As referred to in this disclosure, the term “invertebrate pest” includes arthropods, gastropods and
nematodes, helminths, fungi, bacteria and viruses of economic importance as pests. The term
“arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and
15 symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term
“nematode” refers to a living organism of the Phylum Nematoda. The term “helminths” includes
roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala
and tapeworms (Cestoda).
In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest
20 development (including mortality, feeding reduction, and/or mating disruption), and related
expressions are defined analogously.
The term “agronomic” refers to the production of field crops such as for food, feed and fiber and
includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye,
rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g.,
25 tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree
fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g.,
canola, sunflower, olives).
The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g.,
greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial
30 and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field), wood products,
stored product, agro-forestry and vegetation management, public health (i.e. human) and animal
health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as
wildlife) applications.
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Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by
administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the
present invention, typically in the form of a composition formulated for veterinary use, to the animal
to be protected. As referred to in the present disclosure and claims, the terms “parasiticidal” and
5 “parasiticidally” refers to observable effects on an invertebrate parasite pest to provide protection of
an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity
of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded
growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding
and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including
10 prevention, reduction or elimination) of parasitic infestation or infection of the animal.
The meaning of various terms used in the description shall now be illustrated.
The term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” or -
N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched C1 to C24
alkyl, preferably C1 to C15 alkyl, more preferably C1 to C10 alkyl, most preferably C1 to C6 alkyl. Non15 limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-
methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-
dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-
methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-
dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
20 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and l-ethyl-2-methylpropyl or
the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in
alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be
mono- or polysubstituted identically or differently and independently by alkyl. The same also applies
to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxy, halogen,
25 carbonyl, carbonyloxy and the like, are at the end.
The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to
C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6
alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,
1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2 -propenyl, 2-
30 methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-
butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-
butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,
1,2-dimethyl-2 -propenyl, 1-ethyl-1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-
hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-
35 pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, lmethyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-
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pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,
l,l-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-
dimethyl-1-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-
dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-
5 dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-
ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1-ethyl-l-methyl-2-propenyl, l-ethyl-2-
methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl and the different isomers. “Alkenyl” also includes
polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part
of a composite substituent, for example haloalkenyl and the like, unless defined specifically
10 elsewhere.
Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-
butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, lmethyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl -2-
propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-
15 pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3-
methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, l,l-dimethyl-3-
butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, lethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl and the different isomers. This
definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc.,
20 unless specifically defined elsewhere. The term “alkynyl” can also include moieties comprised of
multiple triple bonds such as 2,5-hexadiynyl.
The term “cycloalkyl” means alkyl closed to form a ring. Non-limiting examples include cyclopropyl,
cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite
substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.