Abstract: This invention relates to 4-substituted phenylamine derivatives of the general formula (I) wherein R1 to R9 and A have the meanings as defined in description. The invention further relates to methods for their preparation and use of said compounds to fight undesired phytopathogenic microorganisms and agents for said purpose comprising said phenylamine derivatives all according to the invention. This invention further relates to a method for fighting undesired phytopathogenic microorganisms by application of said 4-substituted phenylamine derivatives of general formula (I) to such undesired microorganisms and/or to their habitat according to the invention.
The present invention relates to compounds intended to protect crops by fighting undesired phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 4-substituted phenylamine derivatives used to protect crops by fighting undesired phytopathogenic microorganisms.
BACKGROUND OF THE INVENTION
The control of damages to crops caused by phytopathogenic microorganisms is extremely important in achieving high crop efficiency. For instance, plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available to control such damages. The need continues for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action. Certain phenylamine derivatives are disclosed in literature as microbicidally active ingredients in pesticides. For example, WO2000046184, WO2003093224, WO2003024219, WO2005089547, WO2005120234 and US201 10082036 discloses the use of phenylamine derivatives especially phenylamidine, either alone or as part of composition, as fungicides. Certain phenyl benzamides compound, method of producing such compounds and their use for controlling undesired microorganisms is disclosed in WO2004005242.
US4173637 discloses phenylurea compounds and compositions containing these compounds as insecticides. JP08291 146 discloses N-substitued phenylsulfonamide compounds having excellent herbicidal activity, especially paddy field herbicides. WO20081 10314 discloses fluoroalkyl phenylamidines as fungicidal compounds, method of their preparation and a method for protecting seeds from unwanted microorganisms using such compounds. One other PCT publication WO201 1095462 discloses phenylamine derivatives including carboxamides, process for preparaing them and insecticidal, acaricidal, nematicidal or molluscidal compositions comprising these derivatives. Certain amidine compounds exhibiting antifungal activity against pathogenic fungi including fungi of the genera Candida, Aspergillus and Trichophyton, being pharmaceutically useful have been disclosed in WO2013018735.
The effectiveness of the phenylamine 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.
We have now found a new family of compounds which possess the above mentioned effects or advantages. A new family of compounds namely, 4-substituted plienylamine derivatives wherein the phenyl ring is substituted according to the invention thus allowing an unexpected and significantly higher activity against undesired microorganisms such as fungal or bacterial pathogens or pests.
SUMMARY OF THE INVENTION
This present invention relates to a novel and inventive 4-substituted plienylamine derivatives of the general formula (I),
(I)
wherein the definition of the substituents is defined in foregoing detailed description.
The 4-substituted plienylamine derivatives of the present invention are novel and inventive even of US8080688 and its corresponding EP Application No. 2120558.
US8080688 discloses 3,4-disubstituted phenoxyphenyl amidines represented by general formula
wherein two phenyl rings are linked by "-0-".
Please refer Scheme I, Steps (a-f) at page nos. 18-25 compound (I), and Steps (g-j) at page nos. 27-30 compound (I) of US8080688. Also, refer to examples in Table IV page nos. 48-49.
However, in embodiments on page 18, paragraph 5 and claim 4, the applicant of US8080688 has disclosed 3,4-disubstituted benzylphenyl amidines. The list of 3,4-disubstituted benzylphenyl amidines compounds disclosed in US8080688 is reproduced herein below:
N'-[4-(2,3-Dihydro-l H-inden-5-ylmethy])-2,5-dimethy]plienyl]-N-ethyl-N-methylimidofonnami
N'-{4-[(3,3-DimethyI-2,3-dihydro- lH-M
methylimidoformamid,
N'-[4-(3-Chlor-4-isopropylbeiizyl)-2,5-dimethy]phenyl]-N-ethy]-N-rnethy]imidoformamid,
N'-[4-(3-Chlor-4 ert-butylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamid,
N-Ethy]-N'-{4-[(3-hydroxy-3-methyl-2,3-dihydro-l H-inden-5-yl)methyl]-2,5-dimethylphenyl} -N-methylimidoformamid,
N'-[4-(3-Chlor-4-methylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamid,
N'-{2,5-dimethyl-4-[( l , l ,3-trimethyl-2,3-dihydro H-inden-5-yl)methyl]phenyl}-N-ethyl-N-methylimidoformamid,
N'- {2,5-dimethyl-4-[( l , l ,3 rimethyl-2,3-dihydro-l H-inden-5-yl)methyl]phenyl} -N-isopiO^ methylimidoformamid,
N'-{2,5-dimethyl-4-[( l , l ,3-trimethyl-2^
propylimido-formamid,
N'-[2,5-Dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-ylmethyI)phenyl]-N-ethy]-N-methylimidoformamid,
N'-[2,5-Dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-yhnethyl)phenyl]-N-isopropyl-N-methylimidoformamid,
N'-[2,5-Dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)phenyl]-N-methyl-N-propylimidoformamid,
2,5-Dimethyl-N-[( l E)^iperidin- l -ylmethylene]-4-(5,6,7,8-tetra-hydronaphthalen-2-ylmethyl)anilin,
4-(4-tert-butyl-3-chlorobenzyl)-2,5-dimethyl-N-[( l E)- piperidin- l -ylmethylene]anilin,
N'-(4-{3-Chlor-4-[(trimethylsilyl)methyl]benzyl} -2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid,
N'-[4-(3-Chlor-4-isobu1ylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamid,
N'-[4-(4-butyl-3-chlorbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamid,
N42,5-Dimethyl-4-{4-(trifluormethyl)-3-[(trim^
met ylimidoformamid, and
N'-{4-[3-cyclopentyl-4-(trifluormethyl)benzyl]-2,5-dimethylphenyl} -N-ethyl-N-methylimidoform
This disclosure of 3,4-disubstituted benzylphenyl amidines compounds in US8080688 is erroneous and unintentional, for the following reasons: i) that from the language of claim 4, it appears that the applicant intended to claim 3,4-disubstituted phenoxyphenyl amidines and not 3,4-disubstituted benzylphenyl amidines; ii) that 3,4-disubstituted benzylphenyl amidines cannot be prepared by the procedures described in schemes and examples; iii) that in Table IV page nos. 48-49 of US8080688 3,4-disubstituted phenoxyphenyl amidines alone are disclosed.
Thus, in view of this typographical error, which warrants rectification in US8080688 and its corresponding EP Application No. 2120558, the compounds of the present invention are novel.
The inventiveness / non-obviousness of the compounds of the present invention can be seen from the comparative results shown in the example section, wherein it is surprisingly observed that the compounds of the present invention additionally increase the effectiveness for crop protection against attacks by pests, microorganisms, weeds or abiotic stress.
DETAILED DESCRIPTION OF THE INVENTION
Accordingly, the present invention relates to compounds of general formula (I)
(I)
wherein
R1 is selected from the group consisting of hydrogen, CN, SR.", S(0)nR", OR", C-i-n-alkyl, Cj.n-alkoxy, Ci-12.alkyIthio, C2- i 2-aIkenyI, C2-i 2-alkynyl, CM2-haloalkyl, C2_i 2-haloalkenyl, C2_i2-haloaIkynyl, C3.s-cycloalkyl, C4.s-cycloalkenyl, C5.8-cycloalkynyl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)nN, O, and
S(0)„;
R2 and R3 are independently selected from the group consisting of hydrogen, CN, S(0)nR", OR', (C=0)-
R", Ci-n-alkyl, C2.12-alkenyl, C2-i 2-alkynyl,
C2_i2-haloalkenyl, C2-i2-haloalkynyl, C3.8- cycloalkyl, C4.8-cycloalkenyl, C5.8-cycloalkynyl, C5_i8-aryl, C7_i 9-aralkyl, C7.ig-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n; or
R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and wherein each of R1, R2, and R3 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen, X, CN, SCN, SF5, S(0)„R", SiR'3, OR", NR'R", (C=0)-R", CR'=NR", C^-alkyl, C2-12-alkenyl, C2.,2-alkynyl, C,.12- haloalkyl, C2_i -haIoalkenyI, C2.i2-haloaIkynyl, Q.^-haloalkoxy, Ci_i2-haloaIkylthio, C3_g-cycloalkyI, C4. 8-cycloalkenyl, C5.8-cycloalkynyl, C3_8-cycloalkyloxy, C3.8-cycloalkylthio, C5_i8-aryl, C7_i9-aralkyl, C7_i9- alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms ■ selected from the group consisting of N, O, and S(0)„; and all of the groups mentioned above may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or
wherein R4 and R7 or R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and wherein eachof R4, R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R8 and R9 are independently selected from the group consisting of hydrogen, X, CN, SCN, S(0)„R", OS(0)nR",SiR'3, OSiR'3, NR'R", NR'S(0)„R", (C=0)-R", CR'=NR", Q.n-alkyl, C2.12-alkenyl, C2.12- alkynyl, Ci„]2-alkoxy CI.i2-haloalkyl, C2.]2-haloalkenyl, C2.i 2-haloalkynyl, Ci_12-haloalkoxy, C,_i2- haloalkylthio, C3_8-cycloalkyl, C4.8-cycloalkenyl, C5.s-cycloalkynyl, C3.8-cycloalkyloxy, C .8- cycloalkylthio, C5.18-aryl, C7.i 9-aralkyl, C7.) 9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)„; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or wherein
R8 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR' may form a three to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or wherein
R8 and R9 together with the atom to which they are attached may form a group of =C(R'R"'), =S, =NR"';
A is selected from the group consisting of fused or non-fused C6-is-aryl, C5.] 8-heteroaryl, wherein one or more carbon atoms are replaced by heteroatoms selected from N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 optionally substituted by one or more groups of R10; with the proviso that hetroaryl does not represent thiazolyl or thiadiazolyl; wherein
R10 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0),,R", OS(0)nR", NR'S(0)nR", OSiR'3, C,.8-alkyl-S(0)nR", C,.8-alkyl-(C=0)-R", CR'=NR", S(0)„C5.i 8-aryl, S(0)nC7.19-aralkyl, S(0)nC7.19-alkaryl, C,.12-alkyl, C2.12-alkenyl, C2.12-alkynyl, Ci_i2-haloalkyl, C2.] 2-haloalkenyl, C2„] 2-haloalkynyl, Ci.]2-alkoxy, C].i2-alkylthio, CM2-holoalkoxy, C].i2-haloalkylthio,C3.i2-cycloalkyl,C4_8-cycloalkenyl, C5„8-cycloalkynyl, C3.8-cycloalkyloxy, C3.8-cycloalkylthio, C7.i9-aralkyl, C7.i9-alkaryl; bicyclic C5.]2-alkyl, C7.12-alkenyl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
and wherein eachof R8, R9 and R10 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
wherein
X represents halogen;
R' represents hydrogen, straight chain or branched chain Q.n.alkyl or cyclic C3.] 0-alkyl which are optinonally substituted by one or more X;
R" represents hydrogen; NR'2, OR', straight chain or branched chain C 2-alkyl, C^^-haloalkyl, cyclic C3_8-alkyl which are optionally substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2, C5.18-aryl which is optionally substituted by one or more R';
R'" is selected from the groups consisting of hydrogen, R", CN, OR', (C=0)-R', COOR', CONR'2,
straight chain or branched chain C,.12-alkyl, C2.i2-alkenyl, C2„]2-alkynyl; cyclic C3.g-alkyl, C4.8-alkenyl, C5_8-alkynyl; C5_i8-aryl, C7.ig-aralkyl, C7.i9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or
R' and R'" together with the atom to which they are attached or together with further atoms selected from the group consisting of N, O, and S(0)n may form a three to six membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; wherein,
m and n represent integers wherin n=0, 1 or 2; and m = 1 or 2;
According to one other embodiment, compounds of general formula (la) further can be described as
(the)
wherein
Rx and Ry are independently selected from the group consisting of hydrogen, hydroxy, CN, N02, COOR', S(0)nR", OR', (C=0)-R", C,_C12-alkyl, C2.,2-alkenyl, C2.12-alkynyl, C3.8-cycloalkyl, C4-g-cycloalkenyl, C5_8-cycloalkynyl, C5_i8-aryl, C7.i9-aralkyl, C7_]9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n; or
Rx and Ry together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)„, and SiR'2, may form a three to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'2, COOR', CN, and CONR'2;
and wherein all of the groups of Rx and Ry may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
and all other substitutions A and R4 to R10 are as defined in one of the above embodiment.
In one another embodiment preferred substitution, R1 of compound of general formula (I) are of hydrogen, Ci-6-alkyl, Ci.6-alkoxy, Ci„6.alkylthio, Ci.6-haloalkyl, C3_8-cycloalkyl.
In one another embodiment more preferred substitution, R1 of compound of general formula (1) is of hydrogen, Cj.6-alkyl.
In one another embodiment preferred substitution, R2 and R3 of compound of general formula (I) are Q. 6-alkyl, C2-6-alkenyl, C2„6- alkynyl, Ci_6-alkoxy, Ci_6-alkylthio, C|_6-haloalkyl, C3.8-cycloalkyl.
In one another embodiment R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR' and CN.
In one another embodiment preferred ring formation structures with the substitutions R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached are azetidine, pyrrolidine, imidazolidine, oxazolidine, piperidine, morpholine, thiomorpholine, piperazine, 1 -methylpiperazine, 1-methylpyrrolidine, 1-methylpiperidine, 3-methyl-l ,3-thiazinane.
In one another embodiment preferred substitution, R4 and R5 of compound of general formula (I) are of X, CN, S(0)nR", NR'R", (C=0)-R", CR'=NR", C,.6-alkyl, C2.6-alkenyl, Cfi-haloalkyl, d_6-alkoxy, C,.6-haloalkylthio, C3_ -cycloalkyl, C„8-cycloalkylthio.
In one another embodiment preferred substitution, R and R7 of compound of general formula (I) are of hydrogen, X, CN, S(0)„R", NR'R", (C=0)-R", CR'=NR", Ci.5-alkyl, C2.6-alkenyl, C,.6-haloalkyl, C,.6-alkoxy, Ci_6-haloalkylthio, C3_8-cycloalkyl, C3_8-cycloalkylthio.
R4 and R7 or R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and wherein eachof R4, R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2.
In one another embodiment preferred substitution, R8 and R9 on compound of general formula (I) are hydrogen, X, CN, S(0)nR", NR'R", (C=0)-R", CR'=NR", C^-alkyl, C^-haloalkyl, C,.6-alkoxy, C,.6-haloalkoxy, Ci_4-alkylthio, C].6-haloalkylthio, C3.8-cycloalkyl, C3.8-cycloalkoxy, C3_8-cycloalkylthio.
In one another embodiment R8 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S may form a three to six membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2.
In one another embodiment preferred substitution, R10 on compound of general formula (I) are hydrogen X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)„R", Ci.8-alkyl-S(0)nR", C,.6-alkyl-(C=0)-R", CR'=NR", C2_6-alkenyl, C2.6-alkynyl, C,.6-haloalkyl, C2_6-haloalkenyl, Cn-alkoxy, C,.12-alkylthio, Ci.I2-holoalkoxy, Cj.n-haloalkylthio, C3„8-cycloalkyl, C4.8-cycloalkenyl, C3_s-cycloalkyloxy, C3_8-cycloalkylthio.
In one another embodiment two 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 and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to ten membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2.
In one another embodiment preferred A is phenyl, napthalenyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl; substituted with one or more R10.
In one another embodiment more preferred A is phenyl, napthalenyl, thienyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl; substituted with one or more R10.
In one another embodiment wherein R1 to R'° may further optionally substituted by one or more groups selected from the group consisting of X, R", OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
In one another embodiment preferred compound of general formula (I) are
N'-(4-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N,-(4-(3-bromobenzyl)-2-chloro-5-metliylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-biOmobenzyl)-2,5-dimethylphenyl)-N-etliyl-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N '- (2-chloro-4- (2-f! Advise benzyl) -5-iTiethylphenyl) -n-ethyJ-N-methylformiiTiidamide;
N'-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methy]formimidamide;
N'-(2,5-dimethyl-4-(4-(methylsulfinyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylforrnimidamide;
N'-(2-chloiO-4-(3,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-rnethylformiiTiidamide;
N'-(2,5-dimethyI-4-(2-(methyIthio)benzyI)phenyI)-N-ediyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(methylsulfinyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluorobenzyl)-2,5-dimethylpheny])-N-methylformimidamide;
N'-(2-chloro-4-(3-fluoi benzyl)-5-metliylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((Z)-(methylimino)(phenyl)methyl)phenyl)-N-ethyl-N-methylformimidami
N'-(2,5-dimethyl-4-(2-methylbenzy])phenyl)-N-ethy]-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-phenyl-l ,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide;
N-(4-(3-chloro-4-fluorobenzyl)-2,5-diinethylphenyl)-l -morpholinomethanimine;
N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)- l -(piperidin- l -yl)methanimine;
N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)- l -morpho]inomethanimine;
N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-l -(piperidin- l -yl)methanimine;
N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-l -morpholinomethanimine;
N-(2-chloro-4-(3-fluorobenzyl)-5-methyIphenyl)- 1 -(piperidin- 1 -yl)methanimine;
N-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)- l -morpholinomethanimine;
N'-(4-(3-biOmo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide;
N,-(2-chloiO-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylforniimidamide;
N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-mediylformimidamide;
N'-(4-(3-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-nitrobenzyl)phenyI)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-(trifliioromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimida
N-ethyl-N'-(4-(3-fIuoro-5-(trifIuoromethyl)benzyl)-2,5-dimethyIphenyl)-N-methylformimidamide^
N'-(2,5-dimethyl-4-(2-methy]-5-(trifluoromethy])benzyl)phenyl)-N-ethyl-N-methylformii^
N-ethyl-N'-(4-(4-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)- l -morpholinomethanimine;
N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-l-morpholinomethanimine;
N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(4-(2-f!uorobenzyl)-2,5-dimethylphenyl)- 1 -(piperidin- 1 -yl)methanimine;
N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-l-(piperidin-l -yl)methanimine;
N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-l -(piperidin- l -yl)methanimine;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylforrnimidamide
N'-(4-(2-ch]oiObenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylformimidamide
N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-l -morpholinomethanimine;
N-cyano-N'-(4-(2-fluorobenzyl)-2,5-dimeihylphenyl)formimidamide;
N'-(4-(2-chlorobenzy])-2,5-dimethylphenyl)-N-cyanoformimidamide;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;
N'-(4-(2-chloi benzyl)-2,5-dimethylp enyl)-N-isopiOpylformimidamide;
N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylforiTiimidamide;
N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-metlioxybenzyl)-5-methylpheny])-N-et y]-N-methy!formimidamide;
N'-(2-chloro-5-methyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(difluoro(phenyl)methyl)-2-iodo-3,6-dimethy]phenyl)-N-ethyl-N-methy]formimidamide;
N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoiObenzyl)-5-rnethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimida
N'-(2-chloiO-4-(3-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chlorobenzyl)-5-methy]phenyl)-N-ethyl-N-methylforminiidamide;
N'-(2-chloro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;
N-allyl-N'-(4-(2-fluorobenzyl)-2,5-dimediylphenyl)-N-niethylformimidamide;
N-allyl-N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)- l -thiomorpho]inomethanimine;
N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)- l -thiomorpholinomethanimine;
N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethyIphenyl)-N-methylformimidamide;
N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-(cyclopropylmethyl)-N-isopi pylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-cyano-N-(cyanomethyl)formimidamide;
N-cyano-N-(cyanomethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)formimidamide;
N'-(2,5-dimethyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformiinidamide;
N'-(2-chloro-4-(4-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-bis(trifluoromediyl)benzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimediyl-4-(4-(trifluorornediyl)benzy])phenyl)-N-ethyl-N-rnethylformimidaniide;
N'-(2,5-dimethyl-4-(4-(trifluoromediyl)benzyl)phenyl)-N-ethyl-N-iTiethylfoHriimidamide;
N'-(2-chloro-4-(2-chloro-4-fluorobenzyl)-5-mediylphenyl)-N-ethyl-N-methylformimidai'nide;
N'-(2-chloro-4-(2-cyanobenzyl)-5-methyIphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-(trifluoroniethyl)benzyl)phenyl)-N-ethyl-N-methylfomiimidamide; N'-(2-chloro-5-methyl-4-(2-(trifluoromethoxy)benzyl)pheny])-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-methyl-3-(trifluorom
N'-(4-(4-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidami
N'-(4-(3-(l -cyanoediyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-chloro-3-methylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(4-fluoro-3-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-(2-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-(dimethylamino)benzyl)-2,5-dimethy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,3-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,4-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ediyl-N-methylformimidamide;
N'-(2,5-dimediyl-4-(4-(trifluoromedioxy)benzyl)phenyl)-N-ethy]-N-methylformirnidamide;
N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimediylphenyl)-N-ethyl-N-mediylformimidamide;
N'-(2-chloiO-4-(4-fluoro-3-mediylbenzyl)-5-mediylphenyl)-N-ediyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chloro-3-mediylbenzyl)-5-methylphenyl)-N-ediyl-N-methylformimidamide;
(E)-N'-(2-chloro-5-methyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ediyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-met]}ylformimidamide;
N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-mediylformimidamide;
N'-(2-chloro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-mediylformimidamide;
N'-(2-chloro-4-(2-chloro-3-fluorobenzyl)-5-mediylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-chloro-2-fluoiO-5-(trifluoromethyl)benzyl)-5-mediylphenyl)-N-ediyl-N-methylformimidamide;
N'-(4-(cyano(phenyl)methyl)-2,5-dimethylphenyl)-N-ethyl-N-mediylformimidamide;
N'-(2-chloro-4-(2,3-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3,5-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-metliylformimidamide;
N'-(2-chloiO-4-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-niethylformimidamide;
N'-(4-(2-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,3-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloro-2-fluoi -5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloi -5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-(4-chloro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylfonnimidami
N'-(2-chloro-4-(3-fluoro-4-(trinuoromethyl)benzyl)-5-methylphenyI)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-fluoro-4-methylbenzyl)-5-methy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-ch]oro-4-(3-fluoro-5-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-chloro-3-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidam
N'-(4-(2-chloiO-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methy]formimidamide;
N-ethyl-N'-(4-(3-fluoro-4-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-(4-chloro-3-(trifluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylfonnimidamide; N'-(4-(3,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(4-methylbenzyl)phenyl)-N-ethy]-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dich]oro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloi -4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloiO-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-ch]orobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,6-dichloiObenzyl)-2,5-diinethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-bromobenzyl)-2,5-dimethyIphenyl)-N-ethyI-N-methylformimidamide;
N'-(4-(2-chloiO-6-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-metliylformimidamide;
N-ethyl-N'-(4-(3-fluoro-5-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamid
N-ethyl-N'-(4-(5-fluoro-2-methylbenzyl)-2,5-dimethylplienyl)-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-4-(trifluoromethyl)benzyl)-2,5-diniethy]phenyl)-N-methylformimidamide;
N'-(4-(2-chloro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimida N'-(4-(2,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluoiObenzyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chloi benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidam
N'-(2-chloro-4-(3-fluoro-5-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,3-diniethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylforminn'damide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-4-(3-fluorobenzyl)-2-rnethylpheny])-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(2-chloro-4-(3-chloro-5-fluorobenzyl)-5-iTiethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chloro-3-(trifluoromethoxy)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloiO-5-fluotObenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,4-dichlorobenzyl)-5-methy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,4-difluorobenzyl)-5-methyIplienyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methy]formimidami N'-(2,5-dichloro-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-iriethylformimidaniide;
N'-(2,5-dichloro-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-4-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(2-chloro-4-(cyano(4-(trifluoiOmethyl)phenyl)methyl)-5-methylphenyl)-N-ethy]-N-methylformimidamide;
N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(cyano(4-fluorophenyl)methyl)-5-methy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-chloro-4-fluorophenyl)(cyano)inethyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(cyano(p-tolyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((2-chlorophenyl)(cyano)methyI)-5-methylphenyl)-N-ethyl-N-methyIformimidamide
N'-(2-chloro-4-((4-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide
N'-(2-chloro-4-(cyano(3-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-ch]oro-4-(2,6-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide;
N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyc]opropyl-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloiObenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-5-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylpheny])-N-methylformimidamide;
N'-(2,5-dimethyl-4-(pyridin-2-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-iluoro-5-methyI-4-(3-(trifluoiOmethyl)benzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(2-(trifluoiOmethoxy)benzyl)pheny])-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(3-fluoiObenzyl)-5-methylphenyl)-N-methylformimidamide;
N-ethyl-N'-(2-f1uoro-5-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(2-fluoiObenzyl)-5-methylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-((Z)-(methylimino)(o olyl)methyl)phenyl)-N-ethyl-N-methylformimidami
N-ethyl-N'-(4-(3-fluoiObenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N
-methylformimidamide;
methyl N-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)formimidate
N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-3,6-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylfornn^nidamide;
N'-(2-chloro-4-(2-fluoro-6-(trifliioromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimi
N'-(2-cyc]opropyl-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2-cyclopiOpyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamid
N-ethyl-N'-(2-fluoro-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methy]formimidaiTiide;
N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2-fluoro-5-(trifluoromethyl)pheny])-N-ethyl-N-methy]formimidamide;
N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(3-methylbehzyl)-5^
N-ethyl-N'-(2-fluoro-5-(trifluoromethyl)-4-(3-(trifluoromethyl)benzy])phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoiO-4-(3-(trifluoromethoxy)benzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzy])-2-(methylsulfonyl)pheny])forminn'damide;
N-ethyl-N-inethyl-N'-(5-methyl-4-(4-methylbenzyI)-2-(methyIsu]fonyl)phenyI)formimidamide;
N'-(5-chloro-4-(cyano(5-fluoro-2-methylphenyl)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
methyl 2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-chlorophenyl)acetate
N'-(4-( l -(4-bromophenyl)vinyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidarnide;
2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-fluoi phenyl)-N,N-dimethylpropanamide;
2-(2-chloro-4-(((ethyl(methyl)amino)m^
N,N-dimethylacetamide;
N'-(5-chloro-4-((4-chloro-3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoiO-4-(2-fluoiObenzyl)phenyl)-N-ethyl-N-methy]formimidaiTiide;
N'-(4-(3-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methy]formimidamide;
N'-(2,5-difluoro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-4-(2-fluoiObenzyl)-2-methyIphenyI)-N-ethyI-N-methylformimidamide;
N'-(5-cyano-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-5-cyano-2-methy]phenyl)-N-ethy]-N-met]iylformimidamide;
N'-(5-cyano-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-2-iriethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-met]iylformirriidamide;
N'-(5-cyano-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difliioro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-rnethylformimidamide;
N'-(5-chloro-4-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloiO-4-(3-ch]orobenzyl)-2-methylpheny])-N-ethyl-N-metliylformimidamide;
N'-(5-chloro-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-2-methyl-4-(3-methylbenzy])phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloiO-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-niethylformimidamide;
N'-(4-(2-chlorobenzy])-2-cyclopropyl-5-(trifluoromethyI)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylfonnim
N'-(2-cyclopropyl-4-(4-methylbenzyI)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(3-fluoiObenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylforminn^amide;
N'-(2-cyclopiOpyl-4-(4-cyclopropyIbenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformirriidamide;
N'-(2-cyclopropyl-4-(2-methylbenzy])-5-(trifluoromethy])phenyl)-N-ethy]-N-methylformimidamide^
N'-(2,5-difluoiO-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)naphdialen-l -yI)-N-ethyl-N-methylformimidamide;
N-ethyl-N-methyl-N'-(4-(2-methylbenzyl)naphthalen-l -yl)formimidamide;
N'-(2-chloro-4-(cyano(3-(trifluoi methyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide hydrochloride;
N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)fonnimidarnide;
N-ediyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidami
N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)pheny])formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluorornethoxy)benzyl)phenyl)formimidainide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide;
N-ediyl-N-methyl-N'-(5-methyl-4-(2-niethylbenzyl)-2-(methylsulfonyl)phenyl)formimidami
N-ethyl-N-methy]-N'-(5-mediyl-4-(4-methylbenzyl)-2-(mediylsulfony])phenyl)formimidami
N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ediyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluorobenzyl)-5-metliyl-2-(methylsulfonyl)phenyl)-N-methylfonnimidamide;
N-ethyl-N-methyl-N'-(5-methyl-4-(3-niethylbenzyl)-2-(methylsulfonyl)phenyl)forrnimidamide;
N-ediyl-N'-(4-(2-fluorobenzyl)-5-mediyl-2-(mediylsulfonyl)phenyl)-N-methylfonT)imidamide;
N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsidfonyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methy]su]fony])-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide and
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(triiluoromethoxy)benzyl)phenyI)-N-n'iethylformimidaiTiide. * Compound names generated using Chemdraw Professional 16.0
Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.
Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by a person ordinaiy skilled in the art.
Any of the compounds according to the invention, can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors. The invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions. The amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art.
In the above description, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers.
"Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1 , 2-propadienyl and 2,4-hexadienyl.
"Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
"Cyclic alkyl" or "cycloalkyl" includes, for example, cyclopropyl, cyclobiityl, cyclopentyl, and cyclohexyl. Cyclic alkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Cyclic alkynyl similarly refers to cyclic pentynyl, hexynyl, heptynyl and octynyl.
The term "aryl" as used herein is a group that contains any carbon-based aromatic group including, but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like. The aryl group can be substituted or unsubstituted. In addition, the aryl group can be a single ring structure or comprise multiple ring structures that are either fused ring structures or attached via one or more bridging groups such as a carbon-carbon bond.
The term "hetero" in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
The term "heterocyclyl" means a cyclic ring system in which at least one ring atom is not carbon and which can contain heteroatoms independently selected from the group comprising of nitrogen, oxygen, sulfur, phosphorous, boron etc.
The term "heterocyclyl" may be further classified as "non-aromatic heterocyle" and "aromatic heterocycle or heteroaryl".
The term "non-aromatic heterocyle" includes fused or unfused three- to fifteen-membered, preferably three- to tweleve-membered, saturated or fully or partially unsaturated heterocycle, monocyclic or polycyclic (spiro, fused, bridged, nonfused) heterocycle wherein heteroatom is selected from the group of oxygen, nitrogen and sulphur; and if the ring contains more than one oxygen atom, they are not directly adjacent; Non-limiting examples of non-aromatic heterocyle include oxetanyl, oxiranyl; aziridinyl; thiiranyl, azetidinyl, thiethanyl, dithiethanyl, diazetidinyl, 2-tetrahydrofuranyl; 3-tetrahydrofuranyl; 2-tetrahydrothienyl; 3-tetrahydrothienyl; 2-pyrrolidinyl; 3-pyrrolidinyl; 3-isoxazolidinyl; 4-isoxazolidinyl; 5-isoxazolidinyl; 3-isothiazolidinyl; 4-isothiazolidinyl; 2-tetrahydropyranyl; 4-tetrahydropyranyl; . This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl (heterocycle radicals including an alkyl portion as defined above) etc., unless specifically defined elsewhere.
The term "heteroarylaryl" as used herein is a group that contains fused or unfused three to fifteen membered, preferably three to tweleve membered, more preferably 5 or 6 membered; monocyclic or polycyclic unsaturated ring system, containing heteroatoms selected from the group of oxygen, nitrogen, sulphur, phosphorous, boron etc.
Non-limiting examples of 5 membered heteroaryl groups include 2-furyl; 3-furyl; 2-thienyl; 3-thienyl; 2-pyrrolyl; 3-pyrrolyl; 3-isoxazolyl; 4-isoxazolyl; 5-isoxazolyl; 3-isothiazolyl; 4-isothiazolyl; 5-isothiazolyl; 3-pyrazolyl; 4-pyrazolyl; 5-pyrazolyl; 2-oxazolyl; 4-oxazolyl; 5-oxazolyl; 2-thiazolyl; 4-thiazolyl; 5-thiazolyl; 2-imidazolyl; 4-imidazolyl; l,2,4-oxadiazol-3-yl; l,2,4-oxadiazol-5-yl; 1,2,4-thiadiazol-3-yl; l,2,4-thiadiazol-5-yl; l,2,4-triazol-3-yl; l,3,4-oxadiazol-2-yl; l,3,4-thiadiazol-2-yl and l,3,4-triazol-2-yl; 1 -pyrrolyl; 1 -pyrazolyl; 1 ,2,4-triazol-l- yl; 1 -imidazolyl; 1 ,2,3-triazol-l-yl; 1 ,3,4-triazol-l-yl and the like.
Non-limiting examples of 6 membered heteroaryl groups include 2-pyridinyl; 3-pyridinyl; 4-pyridinyl; 3-pyridazinyl; 4-pyridazinyl; 2-pyrimidinyl; 4-pyrimidinyl; 5-pyrimidinyl; 2-pyrazinyl; l,3,5-triazin-2-yl; l,2,4-triazin-3-yl; l,2,4,5-tetrazin-3-yl and the like.
Non-limiting examples of benzofused 5-membered heteroaryl include indol-l-yl; indol-2-yl; indol-3-yl; indol-4-yl; indol-5-yl; indol-6-yl; indol-7-yl; benzimidazol-l-yl; benzimidazol-2-yl; benzimidazol-4-yl; benzimidazol-5-yl; indazol-l-yl; indazol-3-yl; indazol-4-yl; indazol-5-yl; indazol-6-yl; indazol-7-yl; indazol-2-yl; l-benzofuran-2-yl; l-benzofuran-3-yl; l-benzofuran-4-yl; l-benzofuran-5-yl; 1 -benzofuran-6-yl; l-benzofuran-7-yl; l-benzothiophen-2-yl; l-benzothiophen-3-yl; l-benzothiophen-4-yl; 1 -benzothiophen-5-yl; l-benzothiophen-6-yl; l-benzothiophen-7-yl; l,3-benzothiazol-2-yl; 1,3-benzothiazol-4-yl; l,3-benzothiazol-5-yl; l,3-benzothiazol-6-yl; l,3-benzothiazol-7-yl; l,3-benzoxazol-2-yl; l,3-benzoxazol-4-yl; l,3-benzoxazol-5-yl; l ,3-benzoxazoI-6-yl; l,3-benzoxazol-7-yl and the liked.
Non-limiting examples of benzofused 6-membered heteroaryl include quinolin-2-yl; quino!in-3-yl; quinolin-4-yl; quinolin-5-yl; quinolin-6-yl; quinolin-7-yl; quinolin-8-yl; isoquinolin-l-yl; isoquinolin-3-yl; isoquinolin-4-yl; isoqiiinolin-5-yl; isoquinolin-6-yl; isoquinolin-7-yl; isoquinolin-8-yl and the like.
The term "aralkyl" refers to aryl hydrocarbon radicals including an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-napthylhexyl. As used herein, the term "aralkenyl" refers to aryl hydrocarbon radicals including an alkenyl portion, as defined above, and an aryl portion, as defined above. Examples include styryl, 3-(benzyl) prop-2-enyl, and 6-napthylhex-2-enyl.
The term "alkaryl" refers to an aryl group which bears an alkyl group; as used herein, the term "alkaryl" includes both substituted and unsubstituted groups. One example of an alkaryl group is the 4-methylphenyl radical.
"Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
"Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine.
The total number of carbon atoms in a substituent group is indicated by the"Cj-j" prefix where i and j are numbers from 1 to 21. For example, Q-3 alkoxy designates methoxy through propoxy. In the above recitations, when a compound of formula (I) is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1 ) are independently selected from the group of defined substituents. Further, when the subscript indicates a range, e. g. (R) then the number of substituents may be selected from the integers between i and j inclusive.
When a group contains a substituent which can be hydrogen, for example R1 or R2, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
The present invention further relates to a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier. The inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like.
The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compound selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.
The present invention further relates to a composition wherein the concentration of compounds having general formula (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.
The present invention also relates to a method for controlling unwanted microorganisms, wherein compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
The present invention further provides a method for protecting seed against unwanted microorganisms by using seed treated with at least one compound of the formula (I).
The compounds of the formula (I) can possess potent microbicidal activity and can be used for the control of unwanted microorganisms, such as fungi, insects, mites, nematodes and bacteria, in agricultural or horticultural crop protection and in the protection of such materials.
The compounds of the formula (I) can possess very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes .
The compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Rhabditida, Dorylaimida, and Tryplonchida.
The compounds of the formula (I) can be used as insecticides in crop protection, for example, for control of Lepidoptera, Coleoptera, Hemiptera, Homoptera, Thysanoptera, Diptera, Orthoptera & Isoptera.
The compounds of the formula (I) can be used as acaricides in crop protection, for example, for control of Eriophyoidea, Tetranychoidea, Eupodoidea and Tarsonemidae.
The compounds of the formula (I) can be used as bactericides in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enter obacteriaceae, Corynebacteriaceae and Streptomycetaceae.
The compounds of the formula (I) can be used as herbicides and can be effective against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Monocotyledonous broad-leaved weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species. Dicotyledonous broad-leaved weed species may include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annual side, and also Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial broad-leaved weeds. Harmful plants that occur in rice, such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, can be controlled by the compounds of formula (I).
The compounds of the formula (1) can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
The compounds of the formula (I) can be used for controlling or preventing against phytopathogenic fungi, bacteria, insects, nematodes, mites of agricultural crops and or horticultural crops.
The compounds of the formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus 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.
According to the invention, as defined above a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed. The carrier, which may be solid or liquid, are generally inert and should be suitable for use in agriculture.
Useful solid carriers include for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example a!kylary] polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Additionally, suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.
The active ingredients can be applied as such or converted to the customary formulations or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, fertilizers and also microencapsulations in polymeric substances. Application is accomplished in a customary manner, for example by watering, spraying, atomizing, nursery boxes, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It is also possible to treat the seed of the plants.
The active ingredients can be further converted to the nanoformulation with intent to further improve water solubility, thermal stability, bioavailability, sensory attributes, and physiological performance.
Furthermore, the choice of the type of formulation will depend on the specific use.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary thickeners, stickers, gibberellins and also other processing auxiliaries.
The present invention includes not only formulations which are already ready for use and can be deployed
with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.
The auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties. Typical auxiliaries include extenders, solvents and carriers.
Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane, propane, nitrogen and carbon dioxide.
In the formulations it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Further additives may be mineral, vegetable oils and methylated seed oils.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
Compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants. Suitable surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty
esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water. The proportion of surfactants is between 5 and 40 per cent by weight of the inventive composition.
It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Additional components may be stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.
If appropriate, other additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
The formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90% of active ingredient, most preferably between 10 and 70% by weight.
The formulations described above can be used for controlling unwanted microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
Compounds of the formula (I) according to this invention, as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations thereof and can be mixed with known mixing partners in order to broaden, for example, the activity spectrum or to prevent development of resistance. Useful mixing partners include, for example, known fungicides, insecticides, acaricides, nematicides, biopesticides and bactericides. A mixture with other known active ingredients, such as herbicides, or with fertilizers and growth regulators, safeners and/or semiochemicals, is also possible.
Examples for such chemical ingredients are given herein in a not limitating way. Some of them are specified herein by their common names that are known and described, for example in The Pesticide
Manual 17th Ed. , or can be searched in the internet (e.g. under www.alanMOod.net/pesticides). Others are described by their systematic name following the IUPAC rules for nomenclature.
All named mixing partners of the classes (A) to (O) as described below can, if their functional groups enable this, optionally form salts with suitable bases or acids, appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs. They are also understood as being included herein. These examples are
A) Inhibitors of the ergosterol biosynthesis, for example (A01 ) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (A05) cyproconazole, (A06) diclobutrazole, (A07) difenoconazole, (A08) diniconazole, (A09) diniconazole-M, (A 10) dodemorph, (A l l ) dodemorph acetate, (A 12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A15) fenbuconazole, (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A22) flutriafol, (A23) furconazole, (A24) furconazole-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate, (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31 ) myclobutanil, (A32) naftifine, (A33) nuarimol, (A34) oxpoconazole, (A35) paclobutrazol, (A36) pefiirazoate, (A37) penconazole, (A38) piperalin, (A39) prochloraz, (A40) propiconazole, (A41 ) prothioconazole, (A42) pyributicarb, (A43) pyrifenox, (A44) quinconazole, (A45) simeconazole, (A46) spiroxamine, (A47) tebuconazole, (A48) terbinafine, (A49) tetraconazole, (A50) triadimefon, (A51) triadimenol, (A52) tridemorph, (A53) triflumizole, (A54) triforine, (A55) triticonazole, (A56) uniconazole, (A57) uniconazole-p, (A58) viniconazole, (A59) voriconazole, (A60) l-(4-chlorophenyl)-2-(l H-l ,2,4-triazol-l -yl)cycloheptanol, (A61) methyl l -(2,2-dimethyl-2,3-dihydro-lH-inden-l -yl)-lH-imidazole-5-carboxylate, (A62) N'-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl) propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (A63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl} imidoformamide, (A64) 0-[l-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-lH-imidazole-l -carbothioate, (A65) Pyrisoxazole, (A66) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A67) l -{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l ,2,4-triazol-5-yl thiocyanate, (A68) 5-(allylsulfanyl)- l -{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l ,2,4-triazole, (A69) 2-[l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A70) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methy]} -2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A71) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } -2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A72) 1 - { [rel(2R,3 S)-3-(2-chloi phenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l ,2,4-triazol-5-yl thiocyanate, (A73) 1 -{[rel(2R,3R)-3-(2-chlorophenyl)-2 2,4-difluorophenyl)oxiran-2-yl]methyl} H-l ,2,4-triazol-5-yl thiocyanate, (A74) 5-(allylsulfanyl)- l -{[rel(2R,3S)-3-(2-chloroplienyl)-2-(2,4-difluoroplienyl)oxiran-2-yl]methyl}-l H-l ,2,4-triazole, (A75) 5-(allylsulfanyl)-l -{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methyl}- l H-l ,2,4-triazole, (A76) 2-[(2S,4S,5S)- l -(2,4- dichlorophenyl) -5- hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A77) 2-[(2R,4S,5 S)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6 rimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4 riazole-3 hione, (A78) 2-[(2R,4R,5R)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A79) 2-[(2S,4R,5R)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A80) 2-[(2S,4S,5R)- l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethy]heptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A81 ) 2-[(2R,4S,5R)-l-(2,4-dichlorophenyl)-5 iydroxy-2,6,64rimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A82) 2-[(2R,4R,5S)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A83) 2-[(2S,4R,5S)- l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A84) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l -(l H-1 ,2,4-triazol- 1 -yl)propan-2-ol, (A85) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]- 1 -( 1 H-l ,2,4-triazol-l-yl)butan-2-ol, (A86) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l ,2,4-triazol- 1 -yl)pentan-2-ol, (A87) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A88) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-l -(lH-l ,2,4-triazol-l -yl)propan-2-ol, (A89) (2R)-2-( 1 -chlorocyclopropyl)-4-[( 1 R)-2,2-dichlorocyclopropyl]- 1 -( l H-1 ,2,4-triazol- 1 -yl)butan-2-ol,
(A90) (2R)-2-( 1 -chlorocyclopropyl)-4-[( 1 S)-2,2-dichlorocyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A91 ) (2S)-2-( 1 -chlorocyclopropyl)-4-[( 1 S)-2,2-dichlorocyclopropy 1]- 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A92) (2S)-2-( 1 -chlorocyclopropyl)-4-[( 1 R)-2,2-dichlorocyclopropyl]- 1 -( 1 H- 1 ,2,4-triazol- l -yl)butan-2-ol, (A93) (l S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l -(l H- 1 ,2,4-triazol-l -ylmethyl)cyclopentanol, (A94) (lR,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l -(lH-l ,2,4-triazol-l-ylmethyl)cyclopentanol, (A95) 5-(4-chlorobenzyl)-2- (chloromethyl)-2-methyl-l -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol .
B) Inhibitors of the respiratory chain at complex I or II, for example (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (B05) diflumetorim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapyroxad, (B IO) furametpyr, (Bl l) furmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B 13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B14) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B 15) isopyrazam (anti-epimeric enantiomer 1 S,4R,9R), (B 16) isopyrazam (syn-epimeric racemate 1 RS,4SR,9RS), (B 17) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (B18) isopyrazam (syn-epimeric enantiomer 1 S,4R,9S), (B 19) mepronil, (B20) oxycarboxin, (B21 ) penflufen, (B22) penthiopyrad, (B23) pydiflumetofen, (B24) sedaxane, (B25) thifluzamide, (B26) l -methyl-N-[2-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, (B27) 3-(difluoromethyl)-l -methyl-N-[2-(l ,l ,2,2-tetrafluoroethoxy)phenyl]-l H-pyrazole-4-carboxamide, (B28) 3-(difluoromethyl)-N-[4-fIuoro-2-(l , l ,2,3,3,3-hexafluoropropoxy)phenyl]- l -methyl- l H-pyrazoIe-4-carboxamide, (B29) N-[l -(2,4-dichlorophenyl)-l -methoxypropan-2-yl]-3-(difluoiOmethyl)-l -methyl-l H-pyrazole-4-carboxamide, (B30) 5,8-difIuoro-N-[2-(2-fluoro-4-{[4-(trifiuoromethyl)pyridin-2-
yl]oxy}pyhenyl)ethyl]quinazolin-4-amine, (B31 ) benzovindiflupyr, (B32) N-[(l S,4R)-9-(dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5 -yl]-3-(difluoromethyl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, (B33) N-[( l R,4S)-9-(dichloromethylene)-l ,2,3,4-tetrahydro-l ,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-l -methyl- l H-pyrazole-4-carboxamide, (B34) 3-(difluoromethyl)-l -methyl-N-(l , l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazole-4-carboxamide, (B35) ] ,3,5-trimethyl-N-(l ,l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl)-lH-pyrazole-4-carboxamide, (B36) l-methyl-3-(trifluoromethyl)-N-(l , l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazole-4-carboxamide, (B37) l-methyl-3-(trifluoromethyl)-N-[(3R)-l ,l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-1 H-pyrazole-4-carboxamide, (B38) 1 -methyl-3 -(trifluoromethyl)-N- [(3 S)- 1 , 1 ,3 -trimethyI-2,3-dihydro-1 H-inden-4-yl]- 1 H-pyrazole-4-carboxam ide, (B39) 3 -(difluoromethyl)- 1 -methyl-N- [(3 S)- 1 , 1 ,3 -trimethyl-2,3-dihydro-] H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B40) 3-(difluoromethy])-l -methyl-N-[(3R)- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl]-l H-pyrazole-4-carboxamide, (B41 ) 1 ,3,5-trimethyl-N-[(3R)- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl]- 1 H-pyrazole-4-carboxamide, (B42) l ,3,5-trimethyl-N-[(3S)-l ,l ,3- trimethyl-2,3-dihydro- l H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B43) benodanil, (B44) 2-chloro-N-(l , l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl)pyridine-3-carboxamide, (B45) Isofetamid, (B46) l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoiOmethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (B48) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l -methyl-lH-pyrazole-4-carboxamide, (B49) 3 -(difluoromethyl)- 1 -methy 1 -N-[4'-(trifluoromethyl)biphenyl-2-yl]- 1 H-pyrazole-4-carboxamide, (B50) N-(2',5 '-difluorobiphenyl-2-yl)-l -methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, (B51 ) 3-(difluoromethy I)- 1 -methyI-N-[4'-(prop- 1 -yn- 1 -y l)biphenyl-2-yl]- 1 H-pyrazole-4-carboxamide, (B52) 5-fluoro-l ,3-dimethyl-N-[4'-(prop-l -yn-l -yl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B53) 2-chloro-N-[4'-(prop-l -yn-l -yl)biphenyl-2-yl]nicotinamide, (B54) 3-(difluoromethyl)-N- [4'-(3,3-dimethylbut-l-yn-l -yl)biphenyl-2-yl]-l -methyl-lH-pyrazole-4-carboxamide, (B55) N-[4'-(3,3-dimethylbut-l -yn-l -yl)biphenyl-2- yl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, (B56) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)- l -methyl- lH-pyrazole-4-carboxamide, (B 57) N-(4 ' -ethynylbipheny 1-2-y 1 )-5 -fluoro- 1 ,3 -dimethyl- 1 H-pyrazole-4-carboxamide, (B58) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (B59) 2-chloro-N-[4'-(3,3-dimethylbut-l -yn-l -yl)biphenyl-2-yl]nicotinamide, (B60) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-l ,3-thiazole-5-carboxamide, (B61 ) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-l -yn-l-yl)biphenyl-2-yl]-l ,3-dimethyl-l H-pyrazole-4-carboxamide, (B62) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-l-yn-l -yl)biphenyl-2-yl]nicotinamide, (B63) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-l-yn-l -yl)biphenyl-2-yl]- l -methyl- l H-pyrazole-4-carboxamide, (B64) 5-fluoro-N-[4'-(3-methoxy-3-methylbLit-l -yn-l -yl)biphenyl-2-yl]-l ,3-dimethyl-lH-pyrazole-4-carboxamide, (B65) 2-chloro-N-[4'-(3-methoxy-3-methylbut-l -yn-l -yl)biphenyl-2-yl]nicotinamide, (B66) l ,3-dimethyl-N-(l , l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl)-l H-pyrazole-4-carboxamide, (B67) l ,3-dimethyl-N-[(3R)-l ,l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B68) l ,3-dimethyl-N-[(3S)-l , l ,3-trimethyl-2,3-dihydro-
1 H-inden-4-y 1]- 1 H-pyrazole-4-carboxamide, (B69) 3-(difluoromethyl)-N-methoxy- 1 -methy l-N-[ 1 -(2,4,6-trichlorophenyl)propan-2-yl]-lH-pyrazole-4-carboxamide, (B70) 3-(difluoromethyl)-N-(7-fluoro-1 , 1 ,3-trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, (B71 ) 3 -(difluoromethyl)-N-[(3,R)-7-fluoro-l,l,3-tnmethyl-2,3-dihydro-lH-inden-4-yl]-l-m
4-carboxamide, (B72) 3-(difluoromethyl )-N-[(3S)-7-fluoro-l,l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl]- 1 -methyl- 1 H-pyrazole-4-carboxamide.
C) Inhibitors of the respiratory chain at complex III, for example (CO 1 )
ametoctradin, (C02) amisulbrom, (C03) azoxystrobin, (C04) cyazofamid, (C05) coumethoxystrobin, (C06) coumoxystrobin, (C07) dimoxystrobin, (C08) enoxastrobin, (C09) famoxadone, (CIO) fenamidone, (CI 1 ) fenaminstrobin, (C12) flufenoxystrobin, (C13) fluoxastrobin, (C14) kresoxim-methyl, (CI 5) metominostrobin, (CI 6) mandestrobin, (CI 7) orysastrobin, (CI 8) picoxystrobin, (CI 9) pyraclostrobin, (C20) pyrametostrobin, (C21) pyraoxystrobin, (C22) pyribencarb, (C23) triclopyricarb, (C24) trifloxystrobin, (C25) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide, (C26) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(lE)-l-[3-(trifluoromethyl)pheiiyl]ethylidene} amino)oxy]methyl} phenyl) acetamide, (C27) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({l-[3- (trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl} acetamide, (C28) (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro-2-phenylvinyl]oxy} phenyl)ethylidene] amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (C29) Fenaminostrobin, (C30) 5-methoxy-2-methyl-4-(2-{[({(lE)-l-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H- l,2,4-triazol-3-one, (C31 ) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylate, (C32) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (C33) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C34) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C35) (2E,3Z)-5-{[l -(4-chlorophenyl)-lH-pyrazol-3-yJ]oxy}-2-(methoxyimiiio)-N,3-dimethylpent-3-enamide.
D) Inhibitors of the mitosis and cell division, for example (DOl) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) Albendazole, (D08) pencycuron, (D09) thiabendazole, (D10) thiophanate-methyl, (Dll) thiophanate, (D12) zoxamide, (D13) 5-chloiO-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo[l,5-ajpyrimidine, (D14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl) pyridazine.
E) Compounds capable to have a multisite action, for example (E01) bordeaux
mixture, (E02) captafol, (E03) captan, (E04) chlorothalonil, (E05) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (E08) copper oxychloride, (E09) copper(2+) sulfate, (E10) dichlofluanid, (El 1) dithianon, (E12) dodine, (E13) dodine free base, (E14) ferbam, (E15) fluorofolpet, (El 6) folpet, (El 7) guazatine, (E l 8) guazatine acetate, (E l 9) iminoctadine, (E20) iminoctadine albesilate, (E21 ) iminoctadine triacetate, (E22) mancopper, (E23) mancozeb, (E24) maneb, (E25) metiram, (E26) metiram zinc, (E27) oxine- copper, (E28) propamidine, (E29) propineb, (E30) sulfur and sulfur preparations including calcium polysulfide, (E3 1 ) thiram, (E32) tolylfluanid, (E33) zineb, (E34) ziram, (E35) anilazine.
F) Compounds capable to induce a host defence, for example (F01 ) acibenzolar-S-methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin.
G) Inhibitors of the amino acid and/or protein biosynthesis, for example (G01 ) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin- l -yl)quinoline, (G09)oxytetracycline,(G 10)streptomycin.
H) Inhibitors of the ATP production, for example (HO I) fentin acetate, (H02) fentin chloride, (H03) fentinhydroxide, (H04) silthiofam.
I) Inhibitors of the cell wall synthesis, for example (101 ) benthiavalicarb, (102) dimethomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamid, (106) polyoxins, (107) polyoxorim, (108) validamycin A, (109) valifenalate, (110) polyoxin B, (11 1 ) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l -(morpholin-4-yl)prop-2-en-l -one, (112) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -one.
j) Inhibitors of the lipid and membrane synthesis, for example (JO 1 ) biphenyl, (J02) chloroneb, (J03) dicloran, (J04) edifenphos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J10) propamocarb hydrochloride, (Jl l ) prothiocarb, (Jl 2) pyrazophos, (J 13) quintozene, (J14) tecnazene, (J 15) toclofos-methyl.
K) Inhibitors of the melanin biosynthesis, for example (K01 ) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07)tricyclazole.
L) Inhibitors of the nucleic acid synthesis, for example (L01 ) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (L05) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazol, (L09) metalaxyl, (L 10) metalaxyl-M (mefenoxam), (Ll l ) ofurace, (L 12) oxadixyl, (L I 3) oxolinic acid, (L 14)octhilinone.
Inhibitors of the signal transduction, for example (M01 ) chlozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazid.
N) Compounds capable to act as an uncoupler, for example (N01 ) binapacryl, (N02) dinocap, (N03) ferimzone, (N04) fluazinam, (N05) meptyldinocap.
O) Further compounds, for example (O01 ) benthiazole, (O02) bethoxazin, (O03) capsimycin, (O04) carvone, (O05) chinomethionat, (O06) pyriofenone (chlazafenone), (O07) cufraneb, (O08) cyflufenamid, (O09) cymoxanil, (O10) cyprosulfamide, (Oi l ) dazomet, (012) debacarb, (013) dichlorophen, (014) dichlobentiazox, (015) diclomezine, (016) difenzoquat, (017) difenzoquat metilsulfate, (018) diphenylamine, (019) ecomate, (020) fenpyrazamine, (021) fenhexamine, (022) flumetover, (023) fluoroimide, (024) flusulfamide, (025) flutianil, (026) fosetyl-aluminium, (027) fosetyl-calcium, (028) fosetyl-sodium, (029) hexachlorobenzene, (030) irumamycin, (031) isothianil, (032) methasulfocarb, (033) methyl isothiocyanate, (034) metrafenone, (035) mildiomycin, (036) natamycin, (037) nickel dimethyldithiocarbamate, (038) nitrothal-isopropyl, (039) oxamocarb, (040) oxyfenthiin, (041) pentachlorophenol and salts, (042) phenothrin, (043) picarbutrazox (044) phosphorous acid and its salts, (045) propamocarb-fosetylate, (046) propanosine-sodium, (047) pyrimorph, (048) pyraziflumid (049) pyrrolnitrine, (050) tebufloquin, (051) tecloftalam, (052) tolnifanide, (053) triazoxide, (054) trichlamide, (055) zarilamid, (056) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-yl 2-methylpropanoate, (057) l -(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-l ,2-oxazol-3-yl]-l ,3 hiazol-2-yl}piperidin-l -yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l -yl]ethanone, (058) 1 -(4- {4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro- 1 ,2-oxazol-3-yl]- 1 ,3-thiazol-2-yl}piperidin-l -yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l -yl]ethanone, (059) oxathiapiprolin, (060) l-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl- l H-imidazole-l -carboxylate, (061 ) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (062) 2,3-dibutyl-6-chlorothieno[2,3-d]pyriinidin-4(3H)-one, (063 ) 2,6-dimethyl-lH,5H.-[l ,4]dithiino[2,3-c:5,6-c']dipyrrole-l ,3,5,7(2H,6H)-tetrone, (064) 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l -yl]- l -(4-{4-[(5R)-5-phenyl-4,5-dihydro-l,2-oxazol-3 thiazol-2-yl}piperidin-l -yl)ethanone, (065) 2-[5-methyl-3-(trifluoromethyl)-l H-pyrazol-l -yl]-l -(4-{4-[(5S)-5-phenyl-4,5-dihydro-l ,2-oxazol-3-yl]-l ,3-thiazol-2-yl}piperidin- l -yl)ethanone, (066) 2-[5-methyl-3-(trifluoromethyl)-l H-pyrazol-]-yl]- l -{4-[4-(5-phenyl-4,5-dihydro- l ,2-oxazol-3-yl)- l,3-thiazol-2-yl]piperidin-l -yl}ethanone, (067) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (068) 2-chloro-5-[2-chloro-l -(2,6-difluoro-4-methoxyphenyl)-4-methyl- lH-imidazol-5-yl]pyridine, (069) 2-phenylphenol and salts, (070) 3-(4,4,5- trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l -yl)quinoline, (071 ) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (072) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (073) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (074) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (075) 5-
amino- l,3,4-thiadiazole-2 -thiol, (076) 5-chloro-N'-phenyl-N'-(prop-2-yn-l-yl)thiophene-2-sulfonohydrazide, (077) 5-f1uoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (078) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (079) 5-methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin-7-amine, (O80) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (081) N'-(4-{[3-(4-chlorobenzyl)-l ,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (082) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl]propanamide, (083) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-l-yloxy)phenyl]propanamide, (084) N-[(5-bromo-3-chloropyridin-2-yl)rnethyl]-2,4-dichloronicotinamide, (085) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, (086) N-[l-(5-biOmo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (087) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,
WE CLAIM
A compound of general formula (I)
(I)
wherein
R1 is selected from the group consisting of hydrogen, CN, SR", S(0)nR", OR", C1.)2-alkyl,
Ci.12.alkylthio, C2.i 2-alkenyl, C2-i 2-alkynyl, Ci.n-haloalkyl, C2.i2-haloalkenyl, C^n-haloalkoxy, Ci.)2-haloalkylthio, C3_8-cycloalkyl, C^-cycloalkenyl, C5_8-cycloalkynyl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n;
R2 and R3 are independently selected from the group consisting of hydrogen, CN, S(0)„R", OR', (C=0)-R", C] _i2-alkyl, C2_i2-alkenyl, C2-i 2-alkynyl, Ci„i2-haloalkyl, C2.i2-haloalkenyl, C2.i2-haloalkynyl, C3_8-cycloalkyl, C4_8-cycloalkeny], C5.8-cycloalkynyl, C5_i8-aryl, C7_i 9-aralkyl, C7_i9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n;
R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)ra and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and
wherein eachof R1, R2, and R3 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R4, R5, R6 and R7 are independently selected from the group consisting of hydrogen, X, CN, SCN, SF5, S(0)nR", SiR'3i OR", NR'R", (C=0)-R", CR'=NR", C,.12-alkyl, C2.12-alkenyl, C2.12-alkynyl, CM 2-haloalkyl, C2_i 2-haloalkenyl, C .i2-haloalkynyl, Ci_i2-haloalkoxy, Ci.i2-haloalkylthio, C3.8-cycloalkyl, C4. 8-cycloalkenyl, C5.8-cycloalkynyl, C3.8-cycloalkyloxy, C3.8-cycloalkylthio, C5.|8-aryl, C7.] 9-aralkyl, C7_]9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms
selected from the group consisting of N, O, and S(0)„; and all of the groups mentioned above may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or
wherein R4 and R7 or R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0),„ and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and wherein eachof R4, R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R8 and R9 are independently selected from the group consisting of hydrogen, X, CN, SCN, S(0)nR", OS(0)nR", SiR'3, OSiR'3, NR'R", NR'S(0)nR", (C=0)-R", CR'=NR", C,.12-alkyl, C2_12-alkenyl, C2.12-alkynyl, Ci_]2-alkoxy, C2.]2-alkenyloxy, C2.]2-alkynyloxy, CM2-haloalkyl, C 2-haloalkenyl, C2.j2-haloalkynyl, C].]2-haloalkoxy, Ci_i2-haloalkylthio, C„8-cycloalkyl, C4.8-cycloalkenyl, C5_8-cycloalkynyl, C .8-cycloalkyloxy, C3.8-cycloalkylthio, C5.iS-aryl, C 9-ara]kyl. C 9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)„; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or wherein
R8 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a three to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or wherein
R8 and R9 together with the atom to which they are attached may form a group of =C(R'R"'), =S, =NR"';
A is selected from the group consisting of fused or non-fused C 8-aryl, C5„i8-heteroaryl, wherein one or more carbon atoms are replaced by heteroatoms selected from N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 optionally substituted by one or more groups of R10; with the proviso that hetroaryl does not represent thiazolyl or thiadiazolyl; wherein
R10 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)nR", OS(0)nR", NR'S(0)nR", OSiR'3, C,.8-alkyl-S(0)nR",
CR'=NR", S(0)nC5.18-aryl, S(0)„C -aralkyl, S(0)„C7.,9-alkaryl, C,.12-alkyl, C2.12-alkenyl, C2.12-alkynyl, Q.^-haloalkyl, C2_i2-haloalkenyl, C 2-haloalkynyl, Q.^-alkoxy, C].12-alkylthio, C,_i2-
1.08
holoalkoxy, Ci.i 2-haloalkylthio,C3.i2-cycloalky] ,C4.8-cycloalkenyl, C5_8-cycloalkynyl, C3.8-cycloalkyloxy, C3.s-cycloalkylthio, C7_i 9-aralkyl, Cy.ig-alkaryl; bicyclic C5.i2-alkyl, bicyclic C7_]2-alkenyl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)„; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or two 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 and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to ten membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
and wherein eachof R8, R9 and R10 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
wherein
X represents halogen;
R' represents hydrogen, straight chain or branched chain Ci_i2-alkyl or cyclic C3.i0-alkyl which are optinonally substituted by one or more X;
R" represents hydrogen; NR'2, OR', straight chain or branched chain Ci_i2-alkyl, Cj.n-haloalkyl cyclic C3_8-alkyl which are optionally substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2> C5.18-aryl which is optionally substituted by one or more R';
R'" is selected from the groups consisting of hydrogen, R", CN, OR', (C=0)-R', COOR', CONR'2, straight chain or branched chain Ci„)2-alkyl, C2.]2-alkenyl, C2.]2-alkynyl; cyclic C3_8-alkyl, C4_8-alkenyl, C5_8-alkynyl; Cs.is-aryl, C7.i9-aralkyl, C7.] 9-alkaryl; where in the cyclic ring system one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(0)n; and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; wherein
R' and R'" together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a three to six membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
wherein,
m and n represent integers wherin n=0, 1 or 2; and m = 1 or 2;
and agronomically acceptable salts, metallic complexes, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides of said compounds.
2) A compound of general formula (I) according to claim 1 wherein the each substituent is independently selected from:
R1 is hydrogen, C lkyl, C]„6-alkoxy, C |.6.alkylthio, Ci.6-haloalkyl, C3_s-cycloalkyl;
R2 and R3 are Ci-6-alkyl, C2.6-alkenyl, C2_12- alkynyl, C].6-alkoxy, Ci_6.alkylthio, Ci_6-haloalkyl, C3.g-cycloalkyl;
R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR' and CN;
R4 and R5 are of X, CN, S(0)nR", NR'R", (C=0)-R", CR'=NR", C,.6-alkyl, C2-6-alkenyl C,.6-haIoalkyl, C].6-haloalkylthio, C3.8-cycloalkyl, C3.8-cycloalkylthio;
R6 and R7 are of hydrogen, X, CN, S(0)nR", NR'R", (C=0)-R", CR'=NR", C^-alkyl, C2„6-alkenyl, C 6-haloalkyl, Ci_6-haloalkylthio, C3„8-cycloalkyl, C3.8-cycloalkylthio;
R4 and R7 or R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR'2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; and wherein eachof R4, R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R8 and R9 are hydrogen, X, CN, S(0)nR", NR'R", OS(0)nR", OSiR'3, NR'S(0)nR", (C=0)-R", CR -NR", C].6-alkyl, C].6-haloalkyl, C .6-alkenyl, CI-4-alkoxy, C2.6-alkenyloxy, C2.6-alkynyloxy, C1.4-haloalkoxy, C].4-alkylthio, Ci-e-haloalkylthio, C3.s-cycloalkyl, C3.8-cycloalkoxy, C3_8-cycloalkylthio or R8 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S may form a three to six membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R10 is X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, OS(0)„R", OSiR'3, NR'S(0)nR", (C=0)-R", S(0)nR", C,.g-alkyl-S(0)nR",
CR'=NR", C2_6-alkenyl, C2.6-alkynyl, C,_6-haloalkyl, C2_6-haIoaIkenyl, Ci.i2-alkoxy, Ci_i2-alkylthio, C].]2-holoaIkoxy, C).12-haloalkyIthio, C _s-cycIoalkyl, C4. 8-cycloalkenyl, C3.8-cycloalkyloxy, C .8-cycloalkylthio; or two 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 and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)in and SiR'2 may form a four to ten membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'a, COOR', CN, and CONR'2;
A is phenyl, napthalenyl, furyl, thienyl, pyrrolyl; is,oxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl; benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, iquinazolinyl, cinnonyl, substituted with one or more R10;
wherein R1 to R10 may further optionally substituted by one or more groups selected from the group consisting of X, R", OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
and agronomically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides of said compounds
3) A compound of general formula (I) according to claim 1 or 2 wherein the each substituent is independently selected from:
R1 is hydrogen or Ci„6-alkyl;
R2 and R3 are C].6-alkyl, C]_6-haloalkyl;
R4 and R5 are of X, CN, S(0)nR', Cl -6-alkyl, C l-6-haloalkyl, C3-8-cycloalkyl;R6 and R7 are of hydrogen, X, C l -6-alkyl, Cl-6-haloalkyl;
R8 and R9 are hydrogen, X, C -alkyl, C -haloalkyl, CM-alkoxy, C].4-haloalkoxy, C]_4-alkylthio, CM-haloalkylthio, C3.8-cycloalkyl, or R8 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S may form a three to four membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
R'° is X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)nR", OS(0)„R", NR'S(0)„R", OSiR'3, Cg-alkyl-SiO R", C,.6-alkyl-(C=0)-R", CR'=NR", SC,.6-alkyl, C2.6-alkenyl, C2.6-alkynyl, d.6-haloalkyl, C2.6-haloalkenyl, C].]2-alkoxy, C]_i2-alkylthio, C^^-holoalkoxy, Ci_] 2-haloalkylthio, C3_8-cycloalkyl, C .8-cycloalkenyl, C3.8-cycloalkyloxy, C3_8-cycloalkylthio or two 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 and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and SiR' may form a four to ten membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
A is phenyl, napthalenyl, thieny,; isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and quinolinyl substituted with one or more R10 ;
wherein R1 to R10 may further optionally substituted by one or more groups selected from the group consisting of X, R", OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2;
and agronomically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides of said compounds
4) A compound according to any one of claims 1 , 2 or 3 wherein compound of general formula (I) are:
N'-(4-benzyl-2,5-dimethylphenyl)-N-ethy]-N-methylformimidamide;
N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(methylsulfinyl)benzyl)phenyl)-N-etlryl-N-methylformimidamide;
N'-(2-chloro-4-(3,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3,5-dichlorobenzyl)-5-iriethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(methy]thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(methylsulfinyl)benzyl)phenyl)-N-ethyl-N-methylformimidairiide;
N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluorobenzyl)-2,5-dimethylphenyI)-N-methyIformimidamide;
N'-(2-chloro-4-(3-fluoi benzyl)-5-metliylphenyl)-N-ethyl-N-mediylfonTiimidamide;
N'-(2,5-dimethyl-4-((Z)-(methylimino)(phenyl)methyl)phenyl)-N-ethyl-N-methylformimidam
N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-phenyl-l ,3-dithiolan-2-yl)phenyl)-N-ethyl-N^iiethylformimidamide;
N-(4-(3-chloiO-4-fluorobenzyl)-2,5-dimethylphenyl)-l -morpholinomethanimine;
N-(4-(3-cliloro-4-fluorobenzyl)-2,5-dimethylphenyl)-l -(piperidin-l-yl)methaniiTiine;
N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-l-morpholinomethanimine;
N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-l-(piperidin-l -yl)methanimine;
N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-l -morpholinoraethanimine;
N-(2-chloro-4-(3 -fluorobenzyl)-5 -methylphenyl)- 1 -(piperidin- 1 -yl)methanimine;
N-(2-ch]oro-4-(2-chlorobenzyl)-5-methy]phenyl)-l -morpholinomethanimine;
N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimediylphenyl)-N-methylfonTiimidamide;
N'-(2-chloro-4-(3-fluoiObenzyl)-5-methylphenyl)-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methy]formimidamide;
N-ethy]-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methy]formimidamide;
N'-(2,5-dimethyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylfomiimidamide;
N'-(4-(3-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(4-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-nitrobenzy])phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-5-(trifluoromethy^
N'-(2,5-dimethyl-4-(2-methyl-5-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidaiTiide;
N-ethyl-N'-(4-(4-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)- l -morpholinomethanimine;
N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-l -morpholinomethanimine;
N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimet ylphenyl)-N-methylformiiTiidaiTiide;
N-(4-(2-fluoiObenzyl)-2,5-dimethylphenyl)-l -(piperidin- l -yl)methanimine;
N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)- l -(piperidin- l -yl)methanimine;
N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)- l -(piperidin-l -yl)methanimine;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylformimidamide;
N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)- l -morpholinomethanimine;
N-cyano-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)formimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-cyanoformimidamide;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopiOpylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;
N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-mediylformimidamide;
N'-(2-chloiO-4-(4-medioxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformiiTiidamide;
N'-(2-chloro-4-(3-methoxybenzyl)-5-methylpheny])-N-ethyl-N-methylforrnimidamide;
N'-(2-chIoro-5-methyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(difluoro(phenyl)methyl)-2-iodo-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-5-methyl-4-(2-nitrobenzyl)phenyl)-N-et]iyl-N-methylformiiTiidamide;
N'-(2-chloro-4-(4-fIuorobenzyl)-5-methylphenyl)-N-ethyI-N-methyIformimidamide;
N'-(2-chloro-5-methyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidann
N'-(2-chloro-4-(3-chlorobenzyl)-5-mediylphenyl)-N-ediyl-N-mediylformimidamide;
N'-(2-chloro-4-(4-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(3-(trifluoromethyl)benzyl)plienyl)-N-ethyl-N-methylforniimidamide;
N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylfonT)imidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;
N-allyl-N'-(4-(2-fluoi benzyl)-2,5-dimetliylplienyl)-N-methylformimidamide;
N-allyl-N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(4-(2-fluorobenzyl)-2,5-dimethylpheny])- l -thiomorpholinomethanimine;
N-(4-(2-chIoi benzyl)-2,5-dimethyIphenyl)-l -thiomorphoIinomethanimine;
N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethy]phenyl)-N-isopropylformimidamide;
N'-(4-(2-chlorobenzy])-2,5-dimethylphenyl)-N-(cyclopropylmethy])-N-isopropylfonnimidamide;
N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-cyano-N-(cyanomethyl)formimidamide;
N-cyano-N-(cyanomethy])-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)formimidamide;
N'-(2,5-dimethyl-4-(4-((tiifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidami
N'-(2,5-dimethyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylfoniiimidamide;
N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-ch]oi o-4-(4-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-niethy]formimidamide;
N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidami
N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylfornn^nidamide;
N'-(2-chloro-4-(2-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimi
N'-(2-chloro-5-methyl-4-(2-(trifluoiOmethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-methyl-3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidam
N'-(4-(4-chloro-3-fluoi benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-(l -cyanoethyl)benzyl)-2,5-dimetliylphenyl)-N-ethyl-N-methylformimidarnide;
N'-(4-(4-ch]oro-3-methylbenzyl)-2,5-dimethylpheny])-N-ethyl-N-methy]formimidamide;
N-ethy]-N'-(4-(4-fluoiO-3-methylbenzyl)-2,5-dimethylphenyl)-N-methy]formimidamide;
N'-(4-(2-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-(diniethylamino)benzy])-2,5-dimethylphenyl)-N-ethyl-N-methylfonnimidamide;
N'-(4-(2,3-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,4-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide
N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoro-3-methylbenzyI)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chloro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(2-methylbenzyl)pheny])-N-ethyl-N-methy]formimidamide;
N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(3-(trifluororaethoxy)benzyI)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethy]-N-methylformimidamide;
N'-(4-(cyano(phenyl)methyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,3-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(3,5-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-rnethylformimidamide;
N'-(2-chloro-4-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N,-(4-(2-ch]oro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3,5-djfluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylforiTiimidamide;
N'-(4-(2,3-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chloro-5-fluorobenzy])-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chloro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamid Ν'- 2-chloro-4-(3-fluoro-4-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidami Ν'- 2-chloro-4-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethy]-N-methylformimidamide;
Ν'- 2-chloro-4-(3-fluoro-4-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylforrnimidamide;
Ν'- 2-chloro-4-(3-fluoro-5-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
Ν'- 2,5-dichloro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
Ν'- 4-(4-chloro-3-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide Ν'- 4-(2-chloro-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-4-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-(4-chloro-3-(trifluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamid N'-(4-(3,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,6-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chloro-6-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-5-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-(5-fluoro-2-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidam N'-(4-(2-chloro-5-(trifluoromethyl)benzyl)^
N'-(4-(2,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformirnidamide;
N'-(4-(2,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluoi benzyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(5-fIuoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimi
N'-(2-chloro-4-(3-fluoro-5-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,3-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-4-(3-fluoiObenzyl)-2-methylphenyl)-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-rnethylformimidamide;
N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(2-chloro-4-(3-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-chloro-3-(trifluoromethoxy)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N!-(2-chloro-4-(2,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidami
N'-(2,5-dichloro-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dichloro-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-4-(2-fluorobenzyl)-2-methylphenyl)-N-methylformirnidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(2-chloro-4-(cyano(4-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(cyano(3-(trifluoi inethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chioro-4-(cyano(4-fIuorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidami
N'-(2-chloro-4-((3-chloro-4-fluorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(cyano(p-tolyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(cyano(3-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,6-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformim
N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N,-(2-cyclopropyl-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-(3-fluoro-5-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-(2-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylforminn^am
N'-(2,5-dimethyl-4-(pyridin-2-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide
N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(2-(trifluoiOmethoxy)benzyl)phenyl)-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-2-fluoiO-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-methylphenyl)-N-rnethylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fIuoro-4-(2-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-((Z)-(methylimino)(o olyl)methyl)phenyl)-N-ethyl-N-methylformi
N-ethyl-N'-(4-(3-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N
-methylformimidamide;
methyl N-(2-bromo-4-(4-biOmobenzyl)-3,6-dimethylphenyl)formimidate
N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-biOmo-3,6-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chioro-4-(2-fluoro-6-(trifluoromethyl)benzyl)-5-methylpheny])-N-ethyl-N-methylfonnimi
N'-(2-cyclopiOpyl-4-(2-fluoi'obenzyI)-5-methyIphenyl)-N-ethyI-N-methyIformimidamide;
N'-(2-cyclopropyl-5-methyl-4-(4-metliylbenzyl)phenyl)-N-ethyl-N-metliylformimidamide;
N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-5-methyl-4-(3-(trifIuoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidami
N'-(4-(2-chlorobenzyl)-2-fluoro-5-(trif uoromethyl)phenyI)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-(trifluoromethyl)plienyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidaiTiide;
N'-(4-(3-chlorobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylfonnimidamide;
N-ethyl-N'-(2-fluoro-4-(3-fluorobenzy])-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-5-(trifluoiOmethyl)-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide;
N-ethyl-N'-(2-fluoro-4-(3-(trifluoi inethoxy)benzyl)-5-(trifluoi methyl)phenyl)-N-methylformimidamide;
N-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzyl)-2-(methylsu]fonyl)phenyl)formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-4-(4-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;
N'-(5-chloro-4-(cyano(5-fluoi -2-methy!phenyl)methyl)-2-methylp enyl)-N-ethyl-N-methylformimidamide;
methyl 2-(2-chloiO-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-chlorophenyl)acetate;
N'-(4-( l -(4-bromophenyl)vinyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylpheiiyl)-2-(3-fluoropheny])-N,N-dimethylpropanamide;
2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(5-fluoro-2-methylphenyl)-N ,N-d imethylacetamide;
N'-(5-chloro-4-((4-chloi -3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylfoririiniidamide;
N'-(4-(3-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(3-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-cyano-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-4-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-4-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(5-chloro-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamid
N,-(4-(3-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidam
N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(4-cyclopropylbenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cyclopropyl-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-difluoro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-(2-chlorobenzy])naphthalen-l -yl)-N-ethyl-N-methyIformimidamide;
N-ethy]-N-methyI-N'-(4-(2-methylbenzyl)naphthalen-l-yl)formimidamide;
N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-rnethylphenyl)-N-ethyl-N-methylformimidamide; hydrochloride;
N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;
N-ethyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidam
N-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-4-(4-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidan^'^
N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide
N-ethyl-N'-(4-(3-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-metlrylformimidami
N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;
N-ethyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide;
N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-metlrylformimida
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide;
N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide
N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylforminn'damide^ and agronomically acceptable salts, isomers/structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides of said compounds
5) A composition for controlling or preventing against phytopathogenic microorganisms, comprising a compound of general formula (I) according to any of above claims and one or more inert carriers.
6) Compositions comprising compounds of general formula (I) according to any of above claims and or one or more active compatible compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and or mixtures thereof.
7) Compositions according to claim 5 or 6, wherein the concentration of compounds having general
formula (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.
8) Use of compounds of general formula (I) according to any of above claims for the control of phytopathogenic fungi, bacteria, insects, nematodes, mites of agricultural crops and or horticultural crops.
9) Use of compounds of general formula (I) according to claim 1 to 4, or compositions according to any of the claims 5 to 7, for controlling or preventing against phytopathogenic fungi of agricultural crops and or horticultural crops.
10) Use of the compositions according to any of the claims 5 to 7 for controlling or preventing against phytopathogenic fungi, bacteria, insects, nematodes, mites of agricultural crops and or horticultural crops.
1 1) Use of the compounds of general formula (I) according to any of the claims 1 to 4 or compositions according to any of the claims 5 to 7, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus 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.
12) A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and or horticultural crops wherein a compound of general formula (I) according to any of the claim 1 to 4 or compositions according to any of the claims 5 to 7, is applied to the plants, to parts thereof or the locus thereof.
13) A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms in agricultural crops and or horticultural crops wherein a compound of general formula (I) according to any of the claim 1 to 4 or compositions according to any of the claims 5 to 7, is applied to the seeds of plants.
14) A method of controlling or preventing phytopathogenic microorganisms in agricultural crops and or horticultural crops using the compounds of general formula (I) according to any of the claims 1 to 4 or compositions according to any of the claims 5 to 7, which consists in applying effective dosages of compounds or compositions in amounts ranging from 1 g to 5 kg per hectare of agricultural or horticultural crops.
| # | Name | Date |
|---|---|---|
| 1 | 201917014766.pdf | 2019-04-12 |
| 2 | 201917014766-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [12-04-2019(online)].pdf | 2019-04-12 |
| 3 | 201917014766-STATEMENT OF UNDERTAKING (FORM 3) [12-04-2019(online)].pdf | 2019-04-12 |
| 4 | 201917014766-PRIORITY DOCUMENTS [12-04-2019(online)].pdf | 2019-04-12 |
| 5 | 201917014766-FORM 1 [12-04-2019(online)].pdf | 2019-04-12 |
| 6 | 201917014766-FIGURE OF ABSTRACT [12-04-2019(online)].pdf | 2019-04-12 |
| 7 | 201917014766-DECLARATION OF INVENTORSHIP (FORM 5) [12-04-2019(online)].pdf | 2019-04-12 |
| 8 | 201917014766-COMPLETE SPECIFICATION [12-04-2019(online)].pdf | 2019-04-12 |
| 9 | 201917014766-FORM-26 [08-07-2019(online)].pdf | 2019-07-08 |
| 10 | 201917014766-Power of Attorney-090719.pdf | 2019-07-13 |
| 11 | 201917014766-Correspondence-090719.pdf | 2019-07-13 |
| 12 | 201917014766-FORM 3 [27-01-2020(online)].pdf | 2020-01-27 |
| 13 | 201917014766-FORM 18 [23-09-2020(online)].pdf | 2020-09-23 |
| 14 | 201917014766-Proof of Right [12-06-2021(online)].pdf | 2021-06-12 |
| 15 | 201917014766-Information under section 8(2) [12-06-2021(online)].pdf | 2021-06-12 |
| 16 | 201917014766-FORM 3 [12-06-2021(online)].pdf | 2021-06-12 |
| 17 | 201917014766-PETITION UNDER RULE 137 [14-06-2021(online)].pdf | 2021-06-14 |
| 18 | 201917014766-PETITION UNDER RULE 137 [14-06-2021(online)]-1.pdf | 2021-06-14 |
| 19 | 201917014766-OTHERS [14-06-2021(online)].pdf | 2021-06-14 |
| 20 | 201917014766-FER_SER_REPLY [14-06-2021(online)].pdf | 2021-06-14 |
| 21 | 201917014766-CORRESPONDENCE [14-06-2021(online)].pdf | 2021-06-14 |
| 22 | 201917014766-COMPLETE SPECIFICATION [14-06-2021(online)].pdf | 2021-06-14 |
| 23 | 201917014766-CLAIMS [14-06-2021(online)].pdf | 2021-06-14 |
| 24 | 201917014766-ABSTRACT [14-06-2021(online)].pdf | 2021-06-14 |
| 25 | 201917014766-FER.pdf | 2021-10-18 |
| 26 | 201917014766-FORM 3 [11-01-2022(online)].pdf | 2022-01-11 |
| 27 | 201917014766-FORM 3 [02-08-2022(online)].pdf | 2022-08-02 |
| 28 | 201917014766-US(14)-HearingNotice-(HearingDate-27-12-2022).pdf | 2022-12-07 |
| 29 | 201917014766-FORM-26 [26-12-2022(online)].pdf | 2022-12-26 |
| 30 | 201917014766-Correspondence to notify the Controller [26-12-2022(online)].pdf | 2022-12-26 |
| 31 | 201917014766-PETITION UNDER RULE 138 [11-01-2023(online)].pdf | 2023-01-11 |
| 32 | 201917014766-Written submissions and relevant documents [10-02-2023(online)].pdf | 2023-02-10 |
| 33 | 201917014766-MARKED COPIES OF AMENDEMENTS [10-02-2023(online)].pdf | 2023-02-10 |
| 34 | 201917014766-FORM 13 [10-02-2023(online)].pdf | 2023-02-10 |
| 35 | 201917014766-AMMENDED DOCUMENTS [10-02-2023(online)].pdf | 2023-02-10 |
| 36 | 201917014766-Response to office action [03-03-2023(online)].pdf | 2023-03-03 |
| 37 | 201917014766-PatentCertificate16-03-2023.pdf | 2023-03-16 |
| 38 | 201917014766-IntimationOfGrant16-03-2023.pdf | 2023-03-16 |
| 39 | 201917014766-RELEVANT DOCUMENTS [27-09-2023(online)].pdf | 2023-09-27 |
| 1 | 2020-12-1500-25-33E_15-12-2020.pdf |