Abstract: The present invention disclosed 3-substituted phenylamidine compounds of general formula (I), wherein R1, R2, R3, R4, R4a, R4b, A and E have the same meanings as defined in description. The present invention further discloses methods for their preparation and use of the compounds of general formula (I) as a crop protection agent.
The present invention relates to 3-substituted phenylamidine compounds. More particularly, the present invention relates to 3-substituted phenylamidine compounds of general formula (I), to a process for preparation and to a use thereof as a crop protection agent.
BACKGROUND OF THE INVENTION
Fungal pathogens continue to pose a serious threat to public health and agriculture. Therefore, the control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. The plant diseases damage to ornamental, vegetable, field, cereal and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. In addition to often being highly destructive, plant diseases can be difficult to control and may develop resistance to commercial fungicides. Many products are commercially available for these purposes, but the need continues for new fungicidal compounds which are more effective, less costly, less toxic, environmentally safer or have different sites of action.
For example, W02000046184, W02003024219, W02005089547, W02003093224, W02007031507, discloses the phenylamidine derivatives and their use, either alone or as part of compositions, as fungicides.
The effectiveness of phenylamidine derivatives described in the prior art is good, but leaves something to be desired in various cases. Therefore, it is always of high interest in agriculture to use novel pesticidal compounds in order to avoid and/or control the development of microorganisms such as fungal or bacterial pathogens or pests being resistant to known active ingredients. It is therefore of high interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compound to be used, whilst at the same time maintaining an effectiveness at least equivalent to the already known compounds.
Currently, the environmental and economic demands for fungicides are continuously increasing for example with respect to activity spectrum, toxicity, selectivity, application rate, formation of residues and favorable manufacturing processes, and also expand the occurance, for example of resistance problems, therefore there is a continuous need to provide new fungicide compounds which will overcome these environmental and economic requirements and/or alleviate the problems associated with pathogens resistance. Accordingly, the present invention provides a new family of compounds which possesses the above mentioned effects or advantages, thus allowing an unexpected and significantly higher activity
against undesired microorganisms such as fungal or bacterial pathogens.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides a 3-substituted phenylamidine compound of general formula (I) or agriculturally acceptable salts, structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides thereof.
Formula (I)
wherein, R1, R2, R3, R4, R4a, R4b, A and E are as defined in the detailed description.
In an embodiment, the present invention provides a process for preparing a compound of general formula (I) or agriculturally acceptable salt thereof.
In another embodiment, the present invention provides a composition comprising at least one compound of general formula (I) and optionally at least one other active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and or mixtures thereof.
In yet another embodiment, the present invention provides use of compounds of formula (I) and compositions thereof, for controlling and/or preventing phytopathogenic microorganisms of agricultural crops and/or horticultural crops.
In still another embodiment, the present invention provides use of at least one compound of the present invention, in combinations or compositions, and methods of using the same, particularly in the field of agriculture, mainly for protecting plants.
The compounds of the present invention have enhanced activity against microbials, particularly against phytopathogenic fungi. The compounds of the present invention can be applied in the field of agriculture or may be used as intermediates for synthesizing compounds having wider applications.
DF,T ATFFD DESCRIPTION OF THE INVENTION
DEFINITIONS
The following definitions provided 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.
The transitional phrase "comprises", "comprising", "includes", "including", "has", "having", "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.
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.
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 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) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B is 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 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 "pesticide" in each case also always comprises the term "crop protection agent".
The term "undesired microorganisms" or "phytopathogenic microorganisms" such as fungal or bacterial pathogens includes namely Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae respectively.
The term "agronomic" refers to the production of field crops such as for food, fuels, biofuels, any biomaterials and fiber and includes namely 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., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries), biofuel production crops such as com, sugar/starch crops, sugar-beet and sweet sorghum, cellulosic crops such as switchgrass, miscanthus, com stover, poplar, biodiesel crops rapeseed (canola), soybeans, palm oil, mustard, camelina, safflower, sunflower and jatropha 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 and industrial stmctures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), 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.
The terms alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl and heteroaryl groups, as defined herein, are optionally substituted (e.g., "substituted" or "unsubstituted" alkyl, "substituted" or "unsubstituted" alkenyl, "substituted" or "unsubstituted" alkynyl, "substituted" or "unsubstituted" carbocyclyl, "substituted" or "unsubstituted" heterocyclyl, "substituted" or "unsubstituted" aryl or "substituted" or "unsubstituted" heteroaryl group). In general, the term "substituted", whether preceded by the term "optionally" or not, means that at least one hydrogen present on a group (e.g., a carbon or nitrogen atom etc.) is replaced with a permissible substituent, e.g., a substituent which upon substitution results in a stable compound, e.g., a compound which does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, or other reaction under normal conditions (temperature, pressure, air etc.). Unless otherwise indicated, a "substituted" group has a substituent at one or more substitutable positions of the group, and when more than one position in any given structure is substituted, the substituent is either the same or different at each position.
The term " alkyl" , used either alone or in compound words such as " alkyl thio" or "haloalkyl" includes straight-chain or branched Ci to C24 alkyl, preferably Ci to C15 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to G alkyl. Non 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, 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, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
The term " alkenyl" , used either alone or in compound words includes branched or straight -chain C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to G 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-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, l,l-dimethyl-2-propenyl, 1,2-dimethyl- 1-propenyl, l,2-dimethyl-2 -propenyl, 1 -ethyl- 1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl- 3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2 -methyl -4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2 -dime thy 1-1-butenyl, l,2-dimethyl-2-butenyl, l,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-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl- 1-butenyl, l-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 elsewhere.
The term " alkynyl" , used either alone or in compound words includes branched or straight -chain C2 to C24 alkynes, preferably C2 to C15 alkynes, more preferably C2 to C10 alkynes, most preferably C2 to G, alkynes. Non limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3 -methyl -1-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-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, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl,
2-ethyl-3-butynyl and l-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., unless specifically defined elsewhere. "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 but are not limited to cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
The term "cycloalkenyl" means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non limiting examples include but are not limited to cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
The term "cycloalkynyl" means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
claim
1) A compound of formula (I),
wherein,
R1 is selected from the group consisting of hydrogen, cyano, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-C12- alkynyl, Ci-Ci2-haloalkyl, Ci-Ci2-alkoxy, CVCVcycloalkyl and C4-C8-cycloalkylalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S);
R2 is selected from the group consisting of Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, C1-C12- haloalkyl, (C=0)-R" and C¾-CVcycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S); or
R1 and R2 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S) may form a three to seven membered non aromatic ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
each group of R1 and R2 may optionally be substituted with one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
R3 is selected from the group consisting of X, cyano, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci-Ci2-haloalkyl, N(R'R'"), OR", S(0)nR'", (C=0)-R" and CN-CVcycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S);
R4 is selected from the group consisting of X, cyano, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci-Ci2-haloalkyl, N(R'R'"), OR", S(0)„R'", (C=0)-R", C3-C8-cycloalkyl and C7-Ci2-aralkyl; wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S);
R hl and R4b are independently selected from the group consisting of hydrogen, X, cyano, C1-C4- alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, OR", S(0)„R', and CYCYcycloalkyl;
each group of R3 and R4 may optionally be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
A represent -{[C(R6R7)]o-2-(B)o-i }-, -{ [B-C(R6R7)]O-I-C(=Y) }-; wherein B represent O, S, NR5 or CR6R7; and Y represents O or S;
R5 is selected from the group consisting of hydrogen, Ci-C8-alkyl, CYCYalkenyl, CYCYalkynyl, Ci-CYhaloalkyl, S(0)„R'", OR", NR'R", (C=0)-R" and CYCYcycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S);
R6 and R7 are independently selected from the group consisting of hydrogen, X, cyano, C i-Cs-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C8-haloalkyl, N(R")2, OR", (C=0)-R" and C -C8-cycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S); or
R6 and R7 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S) may form a three to six membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
each group of R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
ring E is selected from the group consisting of fused or non-fused C3-Ci8-carbocyclyl and C3-Ci8-heterocyclyl, which may optionally be substituted by one or more groups of R8;
R8 is selected from the group consisting of hydrogen, X, cyano, nitro, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci-Ci2-haloalkyl, C2-Ci2-haloalkenyl, C2-Ci2-haloalkynyl, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C4-C8-cycloalkynyl, C7-Ci9-aralkyl, CYC 12-bicycloal ky I, CYCio-aryl, C3-C6-
heterocyclyl, SCN, SF5, N(R'R'"), OR", S(0)nR'", (C=0)-R"', Ci-C8-alkyl-S(0)nR'', Ci-C8-alkyl-(C=0)-R", CR -NR", -S(R9)=N(R10), -S(R9)(0)=N(R10), S(R9)2=N-, S(R9)2(0)=N- and
S(R9)2(0)=N-C(R6aR7a)-; wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S);
R6a and R7a are independently selected from the group consisting of hydrogen, X, cyano, Ci-C8- alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C8-haloalkyl, C2-C8-haloalkenyl, (NR'')2 OR", S(0)„R"', (C=0)-R" and C3-C8-cycloalkyl; or
R6a and R7" together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S), may form a three to six membered ring, which for its part may be substituted by one or more group selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2; or
R& and R7" together with the atom to which they are attached may form a group of =0 or =S;
R9 is independently selected from the group consisting of Ci-C8-alkyl and C3-C8-cycloalkyl;
R10 is selected from the group consisting of hydrogen, cyano, Ci-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, (C=0)-R", S(0)„R'" and C3-C8-cycloalkyl; or
R9 and R10 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S) may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2; or
R8 and R9 or R10 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S) may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
R5 or R6 or R7 and R8 or two R8 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S), may form a three to ten membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
each group of R8, R9 or R10 may optionally be substituted with one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R'R"), COOR' and CON(R'R");
X represents halogen;
R' is selected from the group consisting of hydrogen, CVCValkyl and C3-C8 -cycloalkyl; wherein alkyl and cycloalkyl group may be optionally substituted by one or more X;
R" is selected from the group consisting of hydrogen, CVCValkyl. CVCVhaloalkyl. C3-C8- cycloalkyl, N(R')2, OR' and CVCV-aryl; wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S);
R'" is selected from the groups consisting of cyano, R", C2-Cs-alkenyl, C2-Cs-alkynyl, C3-C8- cycloalkyl, Ci-CVcycloalkenyl. Ci-Cs-cycloalkynyl. OR', (C=0)-R', COOR', CON(R')2, Ce-Cis- aryl and C7-Ci9-aralkyl; wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S);
each group of R" and R”' may be substituted by one or more groups selected from the group consisting of X, CN, R', OR', SR', N(R')2, COOR' and CON(R')2;
n represents integer 0, 1 or 2;
m represents an integer 0, 1 or 2;
or agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof;
with the proviso that the following compounds are excluded from the definition of compound of formula (I):
N'-(2-cyano-3-((3,3-difluoro-l-methylpiperidin-4-yl)oxy)-5-methoxyphenyl)-N,N- dimethylformimidamide and N'-(5-bromo-2-cyano-3-((2,4-dimethoxybenzyl)oxy)phenyl)-N,N- dimethylformimidamide.
2) The compound of formula (I) as claimed in claim 1, wherein
R1 is selected from the group consisting of CVCValkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, CVCV haloalkyl, CVCValkoxy, CVCVcycloalkyl and C4-Cs-cycloalkylalkyl;
R2 is selected from the group consisting of CVC alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C3-C8- cycloalkyl and CVCVhaloalkyl;
R3 and R4 are independently selected from the group consisting of X, cyano, CVCValkyl, C2-C6- alkenyl, C2-C6-alkynyl, CiWhaloalkyl, N(R'R"'), OR", S(0)nR'", (C=0)-R" and C3-C8-cycloalkyl;
R5 is selected from the group consisting of hydrogen, CVCValkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci- Ce-haloalkyl, CVCVcycloalkyl and OR';
R6 and R7 are independently selected from the group consisting of hydrogen, X, cyano, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl and C3-C4-cycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) or C(=S);
ring E is selected from the group consisting of fused or non-fused C3-Cio-carbocyclyl and C5-C10- heterocyclyl, which may optionally be substituted by one or more groups of R8;
or agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof.
3) The compound of formula (I) as claimed in claim 1, wherein said
R1 and R2 are independently selected from the group consisting of CVCValkyl, C2-Ce-alkenyl, C3-C5- cycloalkyl, and C4-C8-cycloalkylalkyl;
R3 and R4 are independently selected from the group consisting of X, cyano, CVCValkyl, C2-C6- alkenyl, C2-Ce-alkynyl, CVCVhaloalkyl, CVCVcycloalkyl and OR";
R5 is selected from the group consisting of hydrogen, CVCValkyl, CVCValkenyl, CVCValkynyl, CV CVhaloalkyl, CVCVcycloalkyl and OR'.
R6 and R7 are independently selected from the group consisting of hydrogen, X, cyano, CVCValkyl, CVCValkenyl, CVCValkynyl, Ci-CVhaloalkyl, OR') and CVCVcycloalkyl;
ring E is selected from cyclopropyl, cyclobutyl, phenyl, napthalenyl, furyl, thienyl, pyrrolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, iquinazolinyl, cinnonyl, indolizinyl, pyrazolo[l,5-a]pyridinyl, imidazo[l,2-a]pyridinyl, pyrrolo[l,2- ajpyrimidinyl, pyrazolo[l,5-a]pyrimidinyl, imidazo[l,2-a]pyrimidinyl, pyrrolo[l,2-a]pyrazinyl, pyrazolo[l,5-a]pyrazinyl, imidazo[l,2-a]pyrazinyl substituted with one or more R8;
or agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, or N-oxides thereof.
4) The compound of formula (I) as claimed in claim 1, wherein said compound of formula (I) is selected from the group consisting of N'-(2-chloro-5-methyl-3-(p-tolylamino)phenyl)-N-ethyl-N- methylformi midamide, N'-(2,5-dimethyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N- methylformi midamide, N'-(3-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N- methylformi midamide, N'-(2,5-dimethyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N- methylformi midamide, N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N- methylformi midamide, N-ethyl-N'-(3-((2-fluorophenyl)amino)-2,5-dimethylphenyl)-N- methylformi midamide, N-ethyl-N'-(3-((2-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N- methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(phenylamino)phenyl)-N- methylformi midamide, N'-(2-chloro-5-methyl-3-(phenylamino)phenyl)-N-ethyl-N- methylformi midamide, N'-(2-chloro-5-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N- methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N- methylformi midamide, N'-(2-chloro-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N- methylformi midamide, N'-(2-chloro-3-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N- methylformi midamide, N'-(2-chloro-3-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N- methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(o-tolylamino)phenyl)-N- methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((4- ((trifluoromethyl)thio)phenyl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(3- methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4- methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2- fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)- 5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2- (trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-fluorobenzyl)- 5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluorophenyl)amino)-5- methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(o-tolylamino)phenyl)-N- ethyl-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)-2-chloro-5-methylphenyl)-N- ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((4- ((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3- chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3- methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3- fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3- methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-
(m-tolylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((3-chlorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chlorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3- (methyl(m-tolyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((3-isopropylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((4-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-isopropylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N- ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide , N'-(3-((3,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-3-((3,5-difbiorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((2,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(3-((2,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-3-((3,5-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(3-benzyl-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((2,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5 -methyl-3 -(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5 -methyl-3 -((3 -methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(3-(2-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(3-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-
fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylforaiimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3- (methyl(pyridin-2-yl)amino)phenyl)-N-methylforaiimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(3-((2-chloro-5-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylforaiimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2-chloro-5-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-3-methylphenyl)amino)-2-methylphenyl)-N-methylforaii midamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(3-(4-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(4-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(3,4-difluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-
methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-6-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((3- (trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide , N'-(2-chloro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-(trifhioromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-benzyl-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformi midamide, N'-(5-chloro-2-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-bromophenyl)amino)-5-chloro-2-methylphenyl)-N-ethyl-N-
methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b] [1 ,4]dioxin-6-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2- (trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3- (trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-fhioro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4- (trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2- (difhioromethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((2-(trifluoromethyl)benzyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((4-fluoro-3-methylbenzyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-chlorobenzyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b][l,4]dioxin-6-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(5-chloro-2-methyl-3-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(2-bromo-3-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methyl-2-(methylthio)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(o-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((l-(pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((l- (pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-(4-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylforaiimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-methylforaiimidamide, N-ethyl-N'-(5-fbioro-3-(4-fluorobenzyl)-2-methylphenyl)-N-methylforaiimidamide, N'-(3-(3-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-bromo-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-5 -methyl-3 -(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylfonnimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylfonnimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3- (trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(2-chloro-3-((6-ethylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)amino)-5-fluoro-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformi midamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-
methylformimidamide, N'-(3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(4-bromo-2-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-yl(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-methylforaiimidamide, N'-(3-(benzo[d]thiazol-6-yl(methyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4- (methylthio)benzyl)phenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2- (trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2- (trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3- (pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4- (trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3- (trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylfbrmimidamide, N'-(5-chloro-2-methyl-3-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylforaiimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-methylforaiimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformi midamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-
methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)ammo)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((3-fluoro-4-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide , N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((4-fluoro-3-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylforaiimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((4-fbioro-3-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylforaiimidamide , N-ethyl-N'-(5-methoxy-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(3-(3,4-difluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylforaiimidamide, N'-(5-chloro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylforaii midamide, N'-(2-chloro-5-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4- (trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(5-cyano-3-(3-fluorobenzyl)-2-
methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-5-methoxy-2-methylphenyl)-N-ethyl- N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)- N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((2- (trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((2- (trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylforaiimidamide, N'-(2-chloro-5-methyl-3- ((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro- 2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(3-(2-(2- chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N- ethyl-N'-(5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'- (3-(3-cyanobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5- methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide , N'-(3-benzyl- 5-cyano-2-methylphenyl)-N-ethyl-N-methylforaiimidamide , N'-(5-cyano-3-(3-cyanobenzyl)-2- methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-3-(4-fluorobenzyl)-2-methylphenyl)- N-ethyl-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N- methylformimidamide, N'-(5-cyano-2-methyl-3-(3-nitrobenzyl)phenyl)-N-ethyl-N- methylformimidamide, N'-(3-(3-bromobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N- methylformimidamide and N'-(5-cyano-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N- methylformi midamide.
5) A process for preparing the compound of formula (I) as claimed in claim 1, wherein said process comprises at least one of the following steps (a) to (h):
a) converting a compound of formula (XXVI) or (XXIV) to a compound of formula (XXIII) according to the reaction scheme as depicted below:
(XXVI) (XXIV) (XXIII)
b) reacting a compound of formula (XXIII) with a suitable secondary amine (HNR ' R2) to obtain a compound of formula (III) according to the reaction scheme as depicted below:
c) reacting a compound of formula (III) with compound of formula (XII), (XVI), (XVII) or (XXXI) to obtain the compound of formula (I) according to the reaction scheme as depicted below:
d) converting a compound of formula (III) to a compound of formula (II) according to the reaction scheme as depicted below:
e) reacting a compound of formula (II) with a compound of formula (XXX) to obtain a compound of formula (I) according to the reaction scheme as depicted below:
f) reacting a compound of formula (XV) with compound of formula (XII), (XVI), (XVII) or (XXXI) to obtain a compound of formula (XIV) according to the reaction scheme as depicted below:
g) converting a compound of formula (XIV) to a compound of formula (XIII) according to the reaction scheme as depicted below:
(xiv) (xiii)
h) reacting a compound of formula (XIII) with a suitable secondary amine (HNR'R2) to obtain a compound of formula (I) according to the reaction scheme as depicted below:
where in the above reaction schemes, M is selected from the group consisting of lithium derivative, boronic ester, boronic acid, MgX and ZnX.
6) A composition for controlling and/or preventing phytopathogenic microorganisms, comprising a compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts thereof, as claimed in claim 1 and one or more inert carriers.
7) The composition as claimed in claim 6, wherein said composition may additionally comprises one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
8) The composition as claimed in claims 6 or 7, wherein the concentration of compound of formula (I) ranges from 10 to 90% by weight with respect to the total weight of the composition, preferably from
30 to 70% by weight with respect to the total weight of the composition.
9) A combination comprising the compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts thereof as claimed in claim 1 and one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.
10) Use of compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, composition or combination thereof as claimed in claim 1 or 6 or 9, for controlling or preventing agricultural crops and/or horticultural crops against phytopathogenic microorganisms.
11) Use of compounds of formula (I) according to claim 1, or compositions according to claim 6, for controlling rust diseases of agricultural crops and/or horticultural crops.
12) The use of compounds of formula (I) according to claim 11, wherein said rust diseases of crops are Hemileia vastatrix (Coffee rust), Uromyces appendiculatus/fabae/ phaseoli (rust of beans) Puccinia spp. (rusts) on various plants selected from P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. Hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye and Phakopsora spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
13) The use of compounds of formula (I) according to claim 10, wherein phytopathogenic microorganisms are selected from Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and/or horticultural crops.
14) The use of the compound of formula (I) as claimed in claim 10 or 11 or 13, wherein said agricultural crops are cereals, com, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citms and citms trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.
15) A seed comprising compound of formula (I), agriculturally acceptable salts, isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N- oxides or S-oxides thereof as claimed in claim 1, wherein the amount of the compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts thereof is from 0.1 g to 1 kg per 100 kg of seed.
16) A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein said compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, composition or combination thereof as claimed in claim 1 or 6 or 9, is applied to the plants, to parts thereof or to a locus thereof.
17) A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and/or horticultural crops, wherein the compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, composition or combination thereof as claimed in claim 1 or 6 or 9, is applied to the seeds of plants.
18) A method for controlling or preventing phytopathogenic microorganisms in agricultural crops and/or horticultural crops using the compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or
agriculturally acceptable salts, composition or combination thereof as claimed in claim 1 or 6 or 9, which comprises a step of applying an effective dosage of the compound or the composition or the combination, in amounts ranging from 1 g to 2 kg per hectare of agricultural and/or horticultural crops.
19) A method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with the compound of formula (I), isomers/structural isomers, stereo-isomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, composition or combination thereof as claimed in claim 1 or 6 or 9.
20) A compound of formula (A),
Formula (A)
wherein,
Z represent OH, NH2, SH, X, or leaving group;
R1 is selected from the group consisting of Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, C1-C12- haloalkyl, and CVCVcycloalkyl;
R2 is selected from the group consisting of cyano, C2-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci- Ci2-haloalkyl, (C=0)-R", CVCVcycloalkyl and C3-C8-cycloalkyl-Ci-C3-alkyl;
R3 is selected from the group consisting of X, cyano, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci-Ci2-haloalkyl, N(R'R'"), OR", S(0)„R'", (C=0)-R" and CVCVcycloalkyl; wherein one or more carbon atoms in cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S);
R4 is selected from the group consisting of X, cyano, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl, Ci-Ci2-haloalkyl, N(R'R"'), OR", S(0)„R"', (C=0)-R", C3-C8-cycloalkyl and C7-Ci2-aralkyl; wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(0)m and optionally including 1 to 3 ring members selected from the group consisting of C(=0) and C(=S).
21) A compound selected from 2-chloro-5-methyl-N1-(p-tolyl)benzene- 1,3-diamine, 2,5-dimethyl-3-(4- methylbenzyl)aniline, 3-(3-chlorobenzyl)-2,5-dimethylanibne, 2,5-dimethyl-3-(2- methylbenzyl)aniline, 3-(3-fluorobenzyl)-2,5-dimethylaniline, N1-(2-fluorophenyl)-2,5- dimethylbenzene- 1,3 -diamine, N1-(2-fluorophenyl)-N1 ,2, 5-trimethylbenzene- 1,3-diamine, 5-fluoro-2- methyl-N^phenylbenzene- 1,3-diamine, 2-chloro-5-methyl-N1-phenylbenzene-l,3-diamine, 2-chloro- N1 ,5-dimethyl-N1 -phenylbenzene- 1 ,3-diamine, S-lluoro-N1 ,2-dimethyl-N1 -phenylbenzene- 1 ,3- diamine, 2-chloro-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-3-(2-chlorobenzyl)-5-methylanibne, 2-chloro-3-(2-fluorobenzyl)-5-methylaniline, 5-lluoro-2-methyl-Nl -( o-toly I jbenzene- 1 ,3-diamine, 5- fluoro-2-methyl-N1-(4-((trifluoromethyl)thio)phenyl)benzene- 1,3-diamine, 2-chloro-5-methyl-3-(3- methylbenzyl)aniline, 2-chloro-5-methyl-3-(4-methylbenzyl)anibne, 5-lluoro-N1-(2-iluorophenyl)-2- methylbenzene- 1,3 -diamine, N1-(4-(tert-butyl)phenyl)-5-fluoro-2-methylbenzene- 1,3-diamine, 2- chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-fluorobenzyl)-5-methylanibne, 2-chloro-N1-(2-fluorophenyl)-5-methylbenzene- 1,3-diamine, 2-chloro-5-methyl-N1-(o-tolyl)benzene- 1, 3-diamine, N1-(4-(tert-butyl)phenyl)-2-chloro-5-methylbenzene- 1,3-diamine, 2-chloro-5 -methyl -N1- (4-((trifluoromethyl)thio)phenyl)benzene- 1 ,3 -diamine, 2-chloro-3-(3 -chlorobenzyl)-5 -methylanibne,
2-chloro-3-(3-methoxybenzyl)-5-methylaniline, 5-fluoro-N1-(3-fluorophenyl)-2-methylbenzene- 1,3- diamine, 5-fluoro-N1-(3-methoxyphenyl)-2-methylbenzene-l ,3-diamine, 5-fluoro-2-methyl-N1-(m- tolyl)benzene- 1,3 -diamine, 5-fluoro-N1-(3-fluorophenyl)-N1,2-dimethylbenzene- 1,3-diamine, N1-(3- chlorophenyl)-5-fluoro-N1,2-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3-chlorophenyl)-5- methylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(3-fluorophenyl)-5 -methylbenzene- 1 ,3 -diamine, 2-chloro-5- methyl-N^ ^m-toly^benzene- 1,3-diamine, N1-(3-chlorophenyl)-5-fluoro-2-methylbenzene- 1,3- diamine, 5 -fluoro-N1 ,2-dimethyl-N1 -(m-tolyl)benzene- 1,3 -diamine, 5-fluoro-N1-(3-methoxyphenyl)- N1,2-dimethylbenzene- 1 ,3-diamine, 2-chloro-N1-(3-fluorophenyl)-N1 ,5-dimethylbenzene- 1,3- diamine, 2-chloro-N1-(3-chlorophenyl)-N1,5-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3- methoxyphenyl)-5-methylbenzene- 1 ,3-diamine, 2-chloro-N1 ,5-dimethyl-N1 -(m-toly I jbenzene- 1,3- diamine, 2-chloro-3-(4-fluorobenzyl)-5-methylaniline, 3-(2-bromobenzyl)-2-chloro-5-methylanibne, 4-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-(3-amino-2-chloro-5-methylbenzyl)benzonitrile,
3-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-chloro-N1-(3-methoxyphenyl)-N1,5- dimethylbenzene- 1,3 -diamine, 2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 2-chloro-5- methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-chloro-5-methyl-3-(4- (trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 2-chloro- 3-(3-chloro-4-fluorobenzyl)-5-methylanihne, 2-chloro-3-(3,5-dimethylbenzyl)-5-methylaniline, 2- chloro-3-(3-chloro-2-fluorobenzyl)-5-methylaniline, 2-chloro-3-(5-fluoro-2-methylbenzyl)-5- methylaniline, 2-chloro-N1-(3-isopropylphenyl)-5-methylbenzene- 1,3-diamine, 2-chloro-N1-(4-
chlorophenyl)-5-methylbenzene- 1 ,3-diamine, 2-chloro-N1-(4-fluorophenyl)-5-methylbenzene- 1 ,3-diamine, 2-chloro-N1-(4-methoxyphenyl)-5-methylbenzene- 1 ,3-diamine, 2-chloro-N1-(4-chloropheny^-N1, 5 -dimethylbenzene- 1,3 -diamine, 2-chloro-N1-(3-isopropylphenyl)-N1,5-dimethylbenzene- 1,3 -diamine, 2-chloro-N1-(4-methoxyphenyl)-N1,5-dimethylbenzene- 1,3-diamine, 2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylanibne, 2-chloro-5-methyl-3-(pyridin-3-ylmethyl)aniline, 2-chloro-3-(3 ,4-difluorobenzyl)-5-methylanibne, 2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylanibne, 2-chloro-N1-(4-fluorophenyl)-N1,5-dimethylbenzene- 1,3-diamine, 3-benzyl-2-chloro-5-methylanibne, 2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylaniline, 2-chloro-N1 -(3 ,4-difluorophenyl)-5 -methylbenzene- 1 ,3 -diamine, N1-(3 ,4-difluorophenyl)-5 -fluoro-2-methylbenzene- 1 ,3 -diamine, 2-chloro-N1 -( 3, 5-di fluorophenyl j-N1 ,5-dimethylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(2,4-difluorophenyl)-5 -methylbenzene- 1 ,3 -diamine, N1-(2,4-difluorophenyl)-5 -fluoro-2-methylbenzene- 1,3 -diamine, ^-(3, 5-difluorophenyl)-5-fluoro-2-methylbenzene- 1,3-diamine, 2-chloro-N1 -(3 ,5-difluorophenyl)-5 -methylbenzene- 1 ,3 -diamine, 3 -benzyl-5 -chi oro-2-methylanibne, N1-(2,4-difluorophenyl)-5-fluoro-N1,2-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3,4-difluoropheny^-N1 ,5-dimethylbenzene- 1,3 -diamine, 2-chloro-N1-(2,4-difluorophenyl)-N1,5-dimethylbenzene- 1 ,3 -diamine, N1 -(3 ,4-difluorophenyl)-5 -fluoro-N1 ,2-dimethylbenzene- 1 ,3-diamine, N1-(3 ,5 -di fluorophenyl j-S-lluoro-N1 ,2-dimethylbenzene- 1 ,3-diamine, 2-chloro-5-methyl-N1-(pyridin-2-yl)benzene- 1 , 3 -diamine, 2-chloro-5 -methyl-N1 -(3 -methylpyridin-2-yl)benzene- 1 , 3 -diamine, 5 -chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylanibne, 5-chloro-2-methyl-3-(2-methylbenzyl)aniline, 5 -chloro-3-(2-chlorobenzyl)-2-methylaniline, 3 -(2-bromobenzyl)-5 -chloro-2-methylaniline, 2-chloro-3-(2,6-difluorobenzyl)-5-methylanibne, 2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylaniline, 3-(4-bromobenzyl)-2-chloro-5-methylaniline, 5-chloro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-2-methyl-N1-(pyridin-2-yl)benzene- 1,3-diamine, N1-(3-chloro-5-fluorophenyl)-5 -fluoro-2-methylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(3-chloro-5-fluorophenyl)-5 -methylbenzene- 1,3 -diamine, N1-(5-chloro-2-methylphenyl)-5-fluoro-N1,2-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3-chloro-5-fluorophenyl)-N1,5-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(5-chloro-2-methylphenyl)-5-methylbenzene- 1,3-diamine, 5-chloro-3-(3-chlorobenzyl)-2-methylanibne, 5-chloro-3-(3-fluorobenzyl)-2-methylanibne, 5-chloro-3-(2-fluorobenzyl)-2-methylaniline, 2-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(4-methylbenzyl)aniline, N1-(3-chloro-S-fluoropheny^-S-fluoro-N1 ,2-dimethylbenzene- 1,3-diamine, 2-chl oro-N1, 5 -dimethyl -N1- (pyridin-2-yl)benzene- 1,3-diamine, 2-chloro-N1 , 5-dimethyl -N1-(3-methylpyridin-2-yl)benzene- 1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(pyridin-2-yl)benzene-l,3-diamine, 2-chloro-N1-(5-chloro-2-methylpheny^-N^S-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3-fluoro-5-methylphenyl)-5-methylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(5-chloro-3 -methylpyridin-2-yl)-5-methylbenzene- 1,3-
diamine, N1-(2-chloro-5-methylphenyl)-5-fluoro-2-methylbenzene- 1,3-diamine, 5-fluoro-N1-(3-fluoro-5-methylphenyl)-2-methylbenzene- 1,3-diamine, 2-chloro-N1-(2-chloro-5-methylphenyl)-5-methylbenzene- 1,3 -diamine, N1-(5-chloro-2-methylphenyl)-5-fluoro-2-methylbenzene- 1,3-diamine, N1-(2-chloro-5-methylphenyl)-5-fluoro-N1,2-dimethylbenzene-l,3-diamine, 2-chloro-N1-(5-chloro-3-methylpyridin-2-yl)-N1 ,5 -dimethylbenzene- 1 ,3 -diamine, 5-fluoro-N1 -(3-fluoro-5 -methylphenyl)-N^-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(2-chloro-5-methylphenyl)-N1,5-dimethylbenzene-1, 3-diamine, 5-fluoro-N1-(2-fluoro-6-methylphenyl)-2-methylbenzene- 1,3-diamine, 5-fluoro-N1-(2-fluoro-3-methylphenyl)-2-methylbenzene- 1,3-diamine, 2-chloro-N1-(2-fluoro-3-methylphenyl)-5-methylbenzene-1 ,3 -diamine, 5-chloro-3-(4-fluorobenzyl)-2-methylaniline, 3-(4-bromobenzyl)-5-chloro-2-methylanibne, 5-chloro-3-(4-chlorobenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-chloro-3-(3,4-difluorobenzyl)-2-methylanibne, 5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylanibne, 5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-N1-(3- (trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 2-chloro-N1-(2-fluoro-6-methylphenyl)-5-methylbenzene-1 ,3 -diamine, 2-chloro-N1-(4-chloro-2-fluorophenyl)-5-methylbenzene-l ,3-diamine, 2-chloro-5-methyl-N1-(3-(trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, N1-(4-chloro-2-fluorophenyl)-5 -fluoro-2-methylbenzene- 1 ,3 -diamine, 2-chloro-N1-(3 -chloro-5- (trifluoromethyl)phenyl)-5-methylbenzene-l,3-diamine, 2-chloro-N1-(2-fluoro-6-methylphenyl)-N1,5-dimethylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(2-fluoro-3 -methylphenyl j-N1 ,5-dimethylbenzene- 1,3-diamine, N1-(4-chloro-2-fluorophenyl)-5-fluoro-N1,2-dimethylbenzene-l,3-diamine, 5-fluoro-3-(2-fluorobenzyl)-2-methylaniline, 3-(2-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-chlorobenzyl)-5-fluoro-2-methylanibne, 5-fluoro-N1-(2-fluoro-6-methylphenyl)-N1,2-dimethylbenzene- 1,3-diamine, 5-fluoro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-3-(3-fluorobenzyl)-2-methylanibne, 5-fluoro-2-methyl-3-(2-methylbenzyl)aniline, 3-benzyl-5-fluoro-2-methylanibne, 2-chloro-3-(4-methoxybenzyl)-5-methylanibne, 3-(2-bromobenzyl)-5-fluoro-2-methylanibne, 5-fluoro-N1-(2-fluoro-3-methylphenyl)-N1,2-dimethylbenzene- 1,3-diamine, 5-fluoro-N1 , 2-dimethyl -N1 -(3 -(trifluoromethyl)pyri din-2 -yl)benzene- 1 ,3 -diamine, 5 -chloro-2-methyl-N^ ^m-toly^benzene- 1,3-diamine, 5-chloro-2-methyl-Nl -phenylbenzene- 1 ,3-diamine, 2-chloro-N1-(4-chloro-2-fluorophenyl)-N1,5-dimethylbenzene- 1,3-diamine, 2-chloro-N1, 5-dimethyl-N1-(3- (trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 2-chloro-N1-(3-chloro-5- (trifluoromethy^pheny^-N^S-dimethylbenzene- 1,3-diamine, 5-chloro-N1 ,2-dimethyl-N1 -phenylbenzene- 1,3 -diamine, 5 -chi oro-N1, 2-dimethyl -^-(m-toly^benzene- 1,3 -diamine, N1-(3-chloro-5-(trifluoromethyl)phenyl)-5-fluoro-2-methylbenzene- 1,3-diamine, 5-chloro-N1-(4-methoxyphenyl)-2-methylbenzene-l ,3 -diamine, 5-chloro-N1-(3-chlorophenyl)-2-methylbenzene-l ,3-diamine, N1-(3-
bromophenyl)-5-chloro-2-methylbenzene- 1,3-diamine, 5-chloro-N1-(2-fluorophenyl)-2-methylbenzene- 1,3 -diamine, 5-chloro-N1-(3-fluorophenyl)-2-methylbenzene- 1,3-diamine, 5-chloro-N1-(4-methoxyphenyl)-N1,2-dimethylbenzene- 1,3-diamine, 2-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 2-chloro-N1-(2,3-dihydrobenzo[b] [ 1 ,4]dioxin-6-yl)-5-methylbenzene- 1 ,3-diamine, 5-fluoro-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-fluoro-2-methyl-3-(4-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(3- (trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 3-(4-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-N1-(2-(difluoromethoxy)phenyl)-5-methylbenzene- 1,3-diamine, 5-chloro-N1-(2-fluorophenyl)-N1 ,2-dimethylbenzene- 1 ,3-diamine, 5-chloro-N1-(3-fluorophenyl)-N1 ,2-dimethylbenzene- 1,3-diamine, 5-chloro-N1-(3-chlorophenyl)-N1,2-dimethylbenzene-l,3-diamine, 2-chloro-5-methyl-N1-(2-(trifluoromethyl)benzyl)benzene- 1,3-diamine, 5-fluoro-N1-(4-fluoro-3-methylbenzyl)-2-methylbenzene- 1,3 -diamine, 5-chloro-N1-(3-chlorobenzyl)-2-methylbenzene- 1,3-diamine, 2-chloro-N1-(2,3-dihydrobenzo[b][l,4]dioxin-6-yl)-N1,5-dimethylbenzene-l,3-diamine, 5-chloro-2 -methyl -N1-(o-tolyl)benzene- 1,3-diamine, 2-chloro-5-methyl-N1-(pyrimidin-2-yl)benzene-l,3-diamine, 5-f uoro-2-methyl-N1-(pyrimidin-2-yl)benzene- 1,3-diamine, 5-fluoro-2-methyl-3-(4- (trifluoromethyl)benzyl)aniline, 2-bromo-3-(3-fluorobenzyl)-5-methylaniline, 3-(3-fluorobenzyl)-5-methyl-2-(methylthio)aniline, 5-chloro-N1,2-dimethyl-N1-(o-tolyl)benzene-l, 3-diamine, 2-chloro-N1 ,5-dimethyl-N1 -(pyrimidin-2-yl)benzene- 1 ,3 -diamine, 5-fluoro-2-methyl-N1 -(pyrazin-2-yl)benzene- 1,3-diamine, 2-chloro-5 -methyl -N1-(pyrazin-2-yl)benzene- 1,3-diamine, 2-chloro-5-methyl-N'-( I -(pyrazin-2-yl)propan-2-yl)benzene- 1 ,3 -diamine, 2-chloro-5 -methyl -N1 -((5-methylpyrazin-2-yl)methyl)benzene- 1,3-diamine, 5-fluoro-2-methyl-N1-(l-(pyrazin-2-yl)propan-2-yl)benzene- 1 ,3-diamine, 5-fluoro-2 -methyl -N1-((5-methylpyrazin-2-yl)methyl)benzene- 1 ,3-diamine, 5-fluoro-N1, 2-dimethyl -N1-(pyrazin-2-yl)benzene- 1,3-diamine, 5 -f uoro-N1 ,2-dimethyl -N1- (pyrimidin-2-yl)benzene- 1,3-diamine, 5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 4-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-fluoro-3-(4-fluorobenzyl)-2-methylaniline, 3-(3-bromobenzyl)-5-fluoro-2-methylaniline, 3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylaniline, 3 -benzyl-2,5 -dimethylaniline, 2,5-dimethyl-3-(3-methylbenzyl)aniline, 2-bromo-5-methyl-3-(2-methylbenzyl)aniline, 2-chl oro-N1, 5 -dimethyl -N1-(pyrazin-2-yl)benzene- 1,3-diamine, 5-chloro-2-methyl-N1-(pyrazin-2-yl)benzene- 1,3-diamine, 5-chloro-2-methyl-N1 -(pyrimidin-2-yl)benzene- 1 ,3 -diamine , 5 -chi oro-N1, 2-dimethyl-N1 -(pyrazin-2-yl)benzene- 1,3-diamine, 5 -chi oro-N1, 2-dimethyl-N1 -(pyrimidin-2-yl)benzene- 1,3 -diamine, 3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylaniline, 2-chloro-3-(4-fluoro-3-
(trifluoromethyl)benzyl)-5-methylaniline, 3-(2-fluorobenzyl)-2,5-dimethylaniline, 3-(2-chlorobenzyl)-2,5-dimethylanibne, 3-(2-bromobenzyl)-2,5-dimethylanibne, 3-(4-fluorobenzyl)-2,5-dimethylanibne, 3-(4-bromobenzyl)-2,5-dimethylanibne, 3-(4-chlorobenzyl)-2,5-dimethylanibne, N1-(benzo[d]thiazol-6-yl)-5-fluoro-2-methylbenzene-l, 3-diamine, 2-chloro-N1-(6-ethylpyridin-2-yl)-5-methylbenzene- 1,3 -diamine, N1-(6-ethylpyridin-2-yl)-5-fluoro-2-methylbenzene-l,3-diamine, N1-(benzo[d]thiazol-6-yl)-2-chloro-5-methylbenzene- 1,3-diamine, 3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylanibne, 3-(4-bromo-3-methylbenzyl)-5-fluoro-2-methylanibne, 3-(2-bromo- 5-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylaniline, 3-(4-bromo-2-fluorobenzyl)-5-fluoro-2-methylanibne, 5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylanibne, N' -tbenzofdlthiazol- 6-yl j -fluoro-N1 ,2-dimethylbenzene- 1 ,3-diamine, N1-(6-ethylpyridin-2-yl)-5-fluoro-N1,2-dimethylbenzene- 1,3 -diamine, N'-(benzo[d]thiazol-6-yl 1-2-ch loro-N1 ,5-di methyl benzene- 1 ,3-diamine, 5-fluoro-2-methyl-3-(4-(methylthio)benzyl)aniline, N1-(benzo[d]thiazol-6-yl)-5-chloro-2-methylbenzene- 1,3 -diamine, 5-chloro-N1-(6-ethylpyridin-2-yl)-2-methylbenzene- 1,3-diamine, 5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-bromobenzyl)-5-chloro-2-methylanibne,
4-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(2- (trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)anibne, 3-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(4- (methylthio)benzyl)anibne, 5-chloro-N1-(6-ethylpyridin-2-yl)-N1,2-dimethylbenzene- 1,3-diamine, 5-fluoro-N1 -(3-fluoro-4-methoxyphenyl)-2-methylbenzene- 1 ,3 -diamine, 2-chloro-N1 -(3 -fluoro-4-methoxyphenyl)-5-methylbenzene- 1,3-diamine, 5-chloro-N1-(3-fluoro-4-methoxyphenyl)-2-methylbenzene- 1 ,3 -diamine, 5 -fluoro-N1 -(3-fluoro-4-methoxyphenyl)-N1 ,2-dimethylbenzene- 1,3-diamine, 2-chloro-N1-(3-fluoro-4-methoxyphenyl)-N1,5-dimethylbenzene- 1,3-diamine, 5-fhioro-2-methyl-3-(3-nitrobenzyl)aniline, 5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 3-(4-fluorobenzyl)- 5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-methylbenzyl)aniline, 5-methoxy-2-methyl-3- (4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-5-methoxy-2-methylanibne, 3-(2-chlorobenzyl)-5-methoxy-2-methylaniline, 3 -(2-fluorobenzyl)-5 -methoxy-2-methylaniline, 5-chloro-N1 -(3 -fluoro-4-methoxypheny^-N^-dimethylbenzene- 1,3-diamine, 5-methoxy-N1-(2-methoxyphenyl)-2-methylbenzene- 1,3 -diamine, N1-(3-fluoro-4-methoxyphenyl)-5-methoxy-2-methylbenzene-l,3-diamine, 5-methoxy-N1-(2-methoxyphenyl)-N1,2-dimethylbenzene- 1,3-diamine, N1-(3-fluoro-4-methoxyphenyl j-5-methoxy-N1 ,2-dimethylbenzene- 1 ,3-diamine, 5-methoxy-2-methyl-N1-(6- (trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 5-fluoro-2-methyl-N1-(6-
(trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 5-chloro-2-methyl-N1-(6- (trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 2-chloro-N1-(4-fluoro-3-methoxyphenyl)-5-methylbenzene- 1 ,3 -diamine, N1 -(4-fluoro-3 -methoxyphenyl)-5-methoxy-2-methylbenzene- 1,3-diamine, 3-(3-fluorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(3-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-methoxy-2-methylanibne, 5-methoxy-2-methyl-3-(3-nitrobenzyl)anibne, 3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylanibne, 3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylaniline, 2-chloro-5-methyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, N1-(4-fluoro-3-methoxyphenyl)-5-methoxy-N1,2-dimethylbenzene-l,3-diamine, 5-methoxy-N1,2-dimethyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 3-(3,4-difluorobenzyl)-5-methoxy-2-methylaniline, 3-(4-bromobenzyl)-5-methoxy-2-methylanibne, 2-chloro-N1 -(4-fluoro-3 -methoxyphenyl j-N1 ,5-dimethylbenzene- 1 ,3 -diamine, 5-chloro-N1 , 2-dimethyl -N1-(6-(trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(6- (trifluoromethyl)pyridin-2-yl)benzene- 1 ,3-diamine, 5-fluoro-N1 ,2-dimethyl-N1-(6- (trifluoromethyl)pyridin-2-yl)benzene- 1,3-diamine, 3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylaniline, 3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylaniline, 3-(2-bromobenzyl)-5-methoxy-2-methylaniline, 5 -methoxy -2 -methyl-3 -(4-(trifluoromethyl)benzyl)aniline, 5 -methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)anibne, 3-amino-5-(3-fluorobenzyl)-4-methylbenzonitrile, 3-benzyl-5-methoxy-2-methylanibne, 5 -methoxy -2 -methyl-3 -(2-(trifluoromethoxy)benzyl)aniline, 5 -methoxy-2-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene-l,3-diamine, 5-chloro-2-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene- 1 ,3-diamine, 2-chloro-5-methyl-N1-(2- (trifluoromethoxy)phenyl)benzene- 1,3-diamine, 5-fluoro-2-methyl-N1-(2- (trifluoromethoxy)phenyl)benzene- 1,3-diamine, l-(3-amino-5-fluoro-2-methylphenyl)-2-(2-chloro-4-methoxyphenoxy)ethan-l-one, 5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-methoxy-2-methylbenzyl)benzonitrile, 5-methoxy-2-methyl-3-(2- (trifluoromethyl)benzyl)aniline, 3-amino-5-benzyl-4-methylbenzonitrile, 3-amino-5-(3-cyanobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-fluorobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-chlorobenzyl)-4-methylbenzonitrile, 3-amino-4-methyl-5-(3-nitrobenzyl)benzonitrile, 3-amino-5-(3-bromobenzyl)-4-methylbenzonitrile and 3-amino-4-methyl-5-(2-(trifluoromethoxy)benzyl)benzonitrile.
| # | Name | Date |
|---|---|---|
| 1 | 202117026049-FORM 18 [28-12-2022(online)].pdf | 2022-12-28 |
| 1 | 202117026049-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [11-06-2021(online)].pdf | 2021-06-11 |
| 2 | 202117026049-FORM 3 [08-06-2022(online)].pdf | 2022-06-08 |
| 2 | 202117026049-STATEMENT OF UNDERTAKING (FORM 3) [11-06-2021(online)].pdf | 2021-06-11 |
| 3 | 202117026049-Proof of Right [27-04-2022(online)].pdf | 2022-04-27 |
| 3 | 202117026049-PRIORITY DOCUMENTS [11-06-2021(online)].pdf | 2021-06-11 |
| 4 | 202117026049.pdf | 2021-10-19 |
| 4 | 202117026049-FORM 1 [11-06-2021(online)].pdf | 2021-06-11 |
| 5 | 202117026049-DECLARATION OF INVENTORSHIP (FORM 5) [11-06-2021(online)].pdf | 2021-06-11 |
| 5 | 202117026049-FORM-26 [14-09-2021(online)].pdf | 2021-09-14 |
| 6 | 202117026049-COMPLETE SPECIFICATION [11-06-2021(online)].pdf | 2021-06-11 |
| 7 | 202117026049-DECLARATION OF INVENTORSHIP (FORM 5) [11-06-2021(online)].pdf | 2021-06-11 |
| 7 | 202117026049-FORM-26 [14-09-2021(online)].pdf | 2021-09-14 |
| 8 | 202117026049-FORM 1 [11-06-2021(online)].pdf | 2021-06-11 |
| 8 | 202117026049.pdf | 2021-10-19 |
| 9 | 202117026049-PRIORITY DOCUMENTS [11-06-2021(online)].pdf | 2021-06-11 |
| 9 | 202117026049-Proof of Right [27-04-2022(online)].pdf | 2022-04-27 |
| 10 | 202117026049-STATEMENT OF UNDERTAKING (FORM 3) [11-06-2021(online)].pdf | 2021-06-11 |
| 10 | 202117026049-FORM 3 [08-06-2022(online)].pdf | 2022-06-08 |
| 11 | 202117026049-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [11-06-2021(online)].pdf | 2021-06-11 |
| 11 | 202117026049-FORM 18 [28-12-2022(online)].pdf | 2022-12-28 |