Abstract: This invention relates to 4-substituted phenylamine derivatives of the general formula (I) wherein R1 to R8 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 and WO2005120234 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. JP082 1 146 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.
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 phenylamine 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 4-substituted henylamine derivatives of the general formula (I)
(I)
wherein the definition of the substituents is defined in foregoing detailed description.
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", Q.n-alkyl, CM2-alkoxy, C].]2_alkylthio, C2-i 2-alkenyl, C2.]2-alkynyl, C].12-haloalkyl, C2.] 2-haloalkenyl, C2_12-haloalkynyl, C3.s-cycloalkyl,
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)„;
R2 and R are independently selected from the group consisting of hydrogen, CN, S(0)„R", OR', (C=0)-R", C,.12-alkyl, C2-i2-alkenyl, C2-i2-alkynyl, Ci„12-haloalkyl, C2-i2-haloalkenyl, C2-i2-haloalkynyl, C3.8-cycloalkyl, C4_8-cycloalkenyl, C5.s-cycloalkynyl, C5.18-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)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)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'.-,, COOR', CN, and CONR'2; and wherein all of the groups 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", d.12-alkyl, C2-i2-alkenyl, C2-i2-alkynyl, CM 2-haloalkyl, C2.12-haloalkenyl, C2.i2-haloalkynyl, C].]2-haloalkoxy, Ci_12-haloalkylthio, C3.8-cycloalkyl, C _8-cycloalkenyl, C5_8-cycloalkynyl, C _8-cycIoalkyIoxy, C3.8-cycIoalkylthio, C5_i 8-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, 0, 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 all of the groups of 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 is selected from the group consisting of hydrogen, CN, SCN, S(0)„R", SiR'3, NR'R", (C=0)-R", CR -NR", C]_i2-alkyl, C2_]2-alkenyl, C2_i 2-alkynyl, C].j2-haloalkyl, C2.12-haloalkenyl, C2.12-haloalkynyl, C3.8-cycloalkyl, C4_8-cycloalkenyl, C5.8-cycloalkynyl, Cs.i s-aryl, C7_i 9-aralkyl, C7_l 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
A is selected from the group consisting of fused or non-fused C6.]g-aryl, C5.i 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 R9; wherein
R9 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", OSiR'3, NR'S(0)nR", C1-8-alkyl-S(0)nR", C,.g-alkyl-(C=0)-R", CR'=NR", S(0)„C5.18-aryI, S(0)„C7-i 9-aralkyl, S(0)nC7.19-alkaryl, CM2-alkyl, C2.12-alkenyl, C2.12-alkynyl, Ci.12-haloalkyl, C2.i2-haloalkenyl, C2-i 2-haloalkynyl, C]_i2-alkoxy, Ci.n-alkylthio, Ci-]2-holoalkoxy, Ci.n-haloalkylthio, C3.i2-cycloalkyl, C4.s-cycloalkenyl, C5.8-cycloalkynyl, C3.8-cycloalkyloxy, C3.8-cycloalkylthio, C7.i9-aralkyl,
bicyclic C5.]2-alkyl, C7_i2-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; or two R9 together with the atoms to which they attached may form a ring, which may be substituted;
and wherein all of the groups of 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;
wherein
R' represents hydrogen, straight chain or branched chain Cl.]2.alkyl or cyclic C3-10-alkyl which are optinonally substituted by one or more X;
R" represents hydrogen; NR' , OR', straight chain or branched chain C].] 2-alkyl, Cj„]2-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., 8-aryl which is optionally substituted by one or more R';
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 (lb) further can be described as
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-alkyI, C2.12-alkenyl, C2_12-alkynyl, C3.g-cycloalkyl, C4-8-cycloalkenyl, C5.s-cycloalkynyl, C5-i 8-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; 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)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'2, COOR', CN, and CONR'2;
and wherein all other substituents R4 to R9 are as defined in first embodiment.
In one another embodiment preferred substitution, R1 of compound of general formula (I) are of hydrogen, C|.12-alkyl, Ci_] 2-alkoxy, C|.|2.alkylthio, Ci_12-haIoalkyI, C3.8-cycloalkyl;
In one another embodiment more preferred substitution, R1 of compound of general formula (I) is of hydrogen, C].6-alkyl;
In one another embodiment preferred substitution, R2 and R3 of compound of general formula (I) are Ci.,2-alkyl, C2.6-alkenyl, C2.] 2- alkynyl, C 2-alkoxy, C]_12_alkylthio, Ci_12-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)„R", NR'R", (C=0)-R", CR'=NR", C,.12-a]kyl, C2.6-alkenyl, C2.6-alkynyl, CM2-haloalkyl, Ci_]2-haloalkylthio, C3.8-cycloalkyl, C3_8-cycloalkylthio.
In one another embodiment preferred substitution, R6 and R7 of compound of general formula (I) are of hydrogen, X, CN, S(0)nR", NR'R", (CO)-R", CR'=NR", C,.12-alkyl, C2.6-alkenyl, C2.6-alkynyl, CM 2-haloalkyl, C 2-haloalky]thio, C3_8-cycloalkyl, C .8-cycloalkylthio.
In one another embodiment preferred substitution, R8 on compound of general formula (I) is hydrogen, CN, S(0)„R", NR'R", (C=0)-R", CR'=NR", C,.12-alkyl, C2.6-alkenyl, C2_6-alkynyl, C,.12-haloalkyl, C3_ 8-cycloalkyl, C3.6-heterocyclyl, C3_6-heterocyclylalkyl;
In one another embodiment preferred substitution, R9 on compound of general formula (I) are X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)nR", OS(0)„R", OSiR'3, NR'S(0)„R", C,.g-alkyl-S(0)nR", C,_8-alkyl-(C=0)-R", CR'=NR", SC,.,2-alkyl, C2.12-alkenyl, C2.12-alkynyl, CM2-haloalkyl, C2_i2-haloalkenyl, Ci_j2-alkoxy, C^n-alkylthio, C].i2-holoalkoxy, C].12-haloalkylthio, C3-12-cycloalkyl, C4.8-cycloalkenyl, C3.8-cycloalkyloxy, C3.8-cycloalkylthio
In one another embodiment two R9 substitutions 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's, COOR', CN, and CONR'2;
In one another embodiment preferred A is phenyl, napthalenyl, furyl, thienyl, pyrrolyl, thiazolyl, isoxazo'lyl, isothiazolyl, thiadiazolyl, 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 R9
In one another embodiment A is phenyl, napthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl; substituted with one or more R9
In one another embodiment R! to R8 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'-(2,5-dimet yI-4-(phenylamino)phenyl)-N-ethyl-N-methy]formimidaiiiide;
N'-(2,5-dimethyl-4-(methyl(phenyl)amino)phenyl)-N-ethyl-N-metliylformimidamide;
N'-(2-chloro-5-methyl-4-(plienylamino)phenyl)-N-ethyl-N-methylformiiTiidamide;
N'-(2-chloro-5-methy]-4-(methyl(phenyl)aniino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(N-phenylmethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-methyl-4-(perfluoropropan-2-yl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-((3-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-((3,4-dichlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylfornn^nidami N'-(2-chloro-5-methyl-4-(methyl(3,4,5-trifluoi phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(m olyl)ann^o)phenyl)-N-ethyl-N-niethylformimidamide;
N'-(2-chloiO-4-((3,4-dichlorophenyl)(methyl)amino)-5-methyIphenyI)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-5-methyl-4-(methyl(4-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(p olyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-niethyl-4-(N-phenylmethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((2-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((4-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-methoxy-3-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3,4-dimethoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3,5-dimethoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((3-methoxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2,5-dimethyl-4-(methyl(p oly])amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-met oxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylfonninn'dami
N-ethyl-N'-(4-((3-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-(m-tolylamino)phenyl)-N-ethyl-N-methy]formimidamide;
N'-(2,5-dimethyl-4-(p-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(tert-bu1yl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylfonTiimi
N'-(4-((4-(tert-bu1y])phenyl)amino)-2,5-dimethy]phenyl)-N-ethyl-N-methy]formirnidamide;
N'-(4-((2-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluoi phenyl)aiTiino)-2,5-dirnet ylphenyl)-N-methylformimidarnide;
N-ethyl-N'-(4-((2-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-((2-fluorophenyl)(methyl)amino)-5-methy]phenyl)-N-ethyl-N-methy]fonnimidamide
N-ethyl-N'-(4-((3-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((4-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-((2-chlorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-(4-(((ethyl(methyl)amino)methyIene)amino)-2,5-dimethylphenyl)-N-phenylacetamide;
N'-(2-chloro-5-methyl-4-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chlorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-fluoiOphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((2-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((3-fluorophenyl)amino)-2,5-dimethylphenyl)-N-methylformimidarnide;
N'-(2-chloro-4-((2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-chlorophenyl)amino)-5-methy]phenyl)-N-ethyl-N-methylformimidamide;
N-(3-chloiOphenyl)-N,2,5-trimethyI-4-((morphoIinomethylene)amino)aniline;
N'-(2-chloro-4-((3-ch]orophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-(3-Chlorophenyl)-N, 2, 5-trimethyl-4-((piperidin- l -ylmetbylene) amino) aniline;
N-allyl-N'-(4-((3-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-((3-chlorophenyl)(niethyl)amino)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methy]formimidamide;
N'-(4-((3-chloiOphenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethy]-N-methy]forinimidamide;
N'-(2,5-dimethyl-4-(methyl(2-(trifliioiOmethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(trifluoroniethyl)phenyI)ami^io)phenyl)-N-ethyI-N-methyIformimidamide; N'-(2,5-dimethyl-4-((3-(trif!uoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidam N'-(2,5-dimetliyl-4-(methyl(4-(trifluoromet yl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethy]-4-(methyl(3-(trifluoromethoxy)p enyl)amino)phenyl)-N-ethyl-N-met y lfonn imid am i de ;
N'-(2,5-dimethyl-4-((3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-((2-methoxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-met ylformimidamide; N'-(2,5-dimethyl-4-(methyl(3-(methyltM
N'-(2-chloro-5-methyl-4-((3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidaiiiid N'-(2-chloro-5-methyl-4-(m olylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(o-tolylamino)phenyl)-N-ethyl-N-methy]formimidamide;
N'-(2-chloro-4-((4-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylfonTiimidamide;
N'-(2,5-dimethyl-4-(o olylarnino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylfoniiimidamide;
N'-(2-chloro-5-methyl-4-(methyl(o olyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)(methyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimid
N'-(2,5-dimethyl-4-(methyl(o-tolyl)aniino)phenyl)-N-ethyl-N-methylformimidainide;
N'-(2-chloro-4-((2-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((2-(trifluoromethyl)phenyl)amino)pheny])-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethy]-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-fluorophenyl)amino)-5-jnethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-metliylformimidamide; N'-(2,5-dimethyl-4-((3-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-metliylformimidaniide N'-(2-chloi -5-methyl-4-((3-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloi -5-methyl-4-(methyl(3-(tnfluoiOmethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-(trifluoiOmethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,6-difluorophenyl)amino)-2,5-diniethylphenyl)-N-ethyl-N-methylfonTiiiTiidamide;
N'-(2-chloro-4-((2,6-difluoroplienyl)aniino)-5-metliylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,6-difluorophenyl)(methyl)amino)-2,5-dim
N'-(2-chloro-4-((2,6-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-chloro-6-fluorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamid N'-(2-chloro-4-((2-chloro-6-fluorophenyl)amino)-5-met ylphenyl)-N-ethy]-N-met ylformimidamide; N'-(4-((2-chloi -6-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(pentafluoro-16-sulfaneyl)pheny])amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,6-dichIoro-4-(trifluoromethyl)phenyI)amino)-2,5-dimethyIphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethy]-N-methy]formimidamide;
N'-(2-chloro-5-methyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((3-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidami
N'-(2-chloiO-5-methyl-4-((4-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chIoro-5-methyI-4-(methyl(2-(trifluoromethoxy)phenyl)amino)phenyI)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-(trifluoiOmethoxy)phenyl)amino)phenyl)-N-ethy]-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(4-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(3-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(N-phenylethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2,4-dichloro-6-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-(pentafluoro-16-SLilfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloi -4-((2-chloro-6-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-(pentafluoi -16-sulfaneyl)phenyl)arnino)phenyl)-N-ethyl-N-methyl form i m i d am id e;
N'-(2-chloiO-5-methyl-4-(methyl(4-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chIoro-5-methyI-4-(methyl(3-(methyIthio)phenyl)amino)phenyI)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-5-methyl-4-((2-((trifluoiOmethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-((difluoromethyl)thio)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-((difluoromethyl)thio)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethy]-4-((3-((trifluoromethyl)thio)phenyl)amino)pheny])-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-((4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylfonTiimidamide; N'-(2,5-dimethyl-4-(methyl(3-((trifluoi methyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-cliloro-5-met yl-4-(methyl(3-((trifluoromethyl)thio)phenyI)amino)plienyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimetliyl-4-(methyl(4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidam N'-(2-cliloiO-5-methyl-4-(met yl(4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3,5-bis(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylfoniiimidai^ N'-(4-((3,5-bis(trifluoiOmethyl)phenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((3-((trifluoiOmethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-(dimethylamino)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(dimethylamino)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N,-(2-chloro-4-((3-((difluoromethyl)thio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoromethoxy)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N,-(4-((3-(difluoromethoxy)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-(difluoromethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylfoπΉimidamide;
N'-(2,5-diniethyl-4-((2-(ti fluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylfoniiimidamide;
N'-(2-chloro-4-((4-(difluoromethoxy)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-difluorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylfomiimidamide;
N'-(2-chloi -4-((2,5-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide
N'-(4-((3,5-bis(trifluoromethyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3,5-bis(trifluoromethyl)phenyl)(methyl)amino)-2-chloro-5-methylphenyl)-N-ethy]-N-methylformimidamide;
N'-(2,5-dimethyl-4-((5-methyl-2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-difluorophenyl)(methyl)amino)-2,5-dimethy]phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloiO-4-((2,5-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(5-methyl-2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N,-(4-((4-chloro-2-(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chIoro-4-((4-chloiO-2-(trifluoromethyl)phenyl)amino)-5-methyIphenyl)-N-ethyI-N-methylformimidamide;
N'-(4-((4-chloro-2-(trifluoromethyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-chloro-2-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-(difluoromethoxy)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((2-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-chloiO-4-(trifluoromethyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
]SI'-(2-chloro-4-((2-chloro-4-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylfomiimidamide; N-ethyl-NH4 (4-fluoro-3-( l , l ,2,2 etraf uoroethoxy)phenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-((4-fluoro-3-(l , l ,2,2 etrafluoroethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
5-chloro-N-(2-fluorophenyl)-N,2-dimethyl-4-((morpholinomethylene)amino)aniline;
N'-(2-chloro-4-(N-(2-fluorophenyl)methylsulfonamido)-5-methylphenyl)-N-ediyl-N-methylformimidamide;
N-(5-chloi -4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-fluorophenyl)acetamide;
N'-(2-chloro-4-((2-fluorophenyl)(methyl)amiiio)-5-methylphenyl)-N,N-dimethylformimidamide; N'-(2-chloro-4-(ethyl(2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; 5-chloro-N-(2-fluorophenyl)-N,2-dimethyl-4-((inorpholinomethylene)amino)aniline;
5-chloro-N-(2-fluorophenyl)-N,2-dimediyl-4-((thiomorpholinomethylene)amino)aniline;
N-ethy]-N'-(5-fluoiO-4-((4-fluoiO-3-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-ethyl-N,-(5-fluoro-4-((4-fluoiO-3-(l , l ,2,2-tetrafluoroethoxy)phenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(mediyl)amino)methylene)amino)-2-methylphenyl)-N-(2-chlorophenyl)acetamide;
N'-(2-chloro-4-(N-(2-chlorophenyl)methylsulfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-((difluoromethyl)thio)phenyl)amino)-2,5-dimethylpheny])-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-((difluoromethyl)thio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-((difluoromethyl)thio)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyi-N-methylformimidamide;
N'-(2-chloro-4-((4-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(ethyl(phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-(5-ch]oro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-phenylacetamide; N'-(2-chloro-4-((2-((difluoromethyl)thio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(ethyl(3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((3-(difluoi methoxy)-4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(N-(3-methoxyphenyl)methylsulfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoromethoxy)-4-fluorophenyl)amino)-2,5-dimethy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-(difluoromethoxy)-4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoromethoxy)-4-fluorophenyl)(methyl)amino)-2,5-dimethylpheny])-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-dimethylphenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2,5-dimethylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-chlorophenyl)propionamide;
N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl)amino)-2-methylphenyl)-N-methylfonriimidamide; N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-fluorophenyl)propionamide
N'-(2-chloro-4-(N-(4-fluoro-3-( l , l ,2,2-tetrafluoroethoxy)phenyl)methylsulfonamido)-5-methylphenyl)-N-ethy]-N-methylformimidamide;
N,-(2,5-dimethyl-4-((3-( l , l ,2,2-tetrafluoroethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-( l , l ,2,2-tetrafluoroethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluoro-5-methylphenyl)amino)-2,5-dimethylpheriyl)-N-methylformimidamide; N-ethyl-N'-(5-fluoro-4-((2-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluoro-5-methylphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-((2-fluoro-5-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(phenylamino)phenyl)-N-methylformimidamide;
N'-(4-((2-chlorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(tert-butyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(m-tolylamino)phenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methyIene)amino)-2-methyIphenyI)-N-phenylpropionamide; N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(3-methoxyphenyl)acetamide
N'-(2-chloro-4-((4-fluoiO-3-methoxypheny])amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-metliy]formimidamide; N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl)(iTiethyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-((2-((difluoromethyl)thio)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-((difluoiOmethyl)thio)phenyl)(methyI)amino)-2,5-diiTiethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-6-fluoro-3-methy]-4-(phenylamino)phenyl)-N-ethyl-N-methylformiiriidamide;
N'-(2-chloro-5-methyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-6-fluoro-3-methyl-4-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-((l -methylindolin-5-yl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(methyl(phenyl)amino)phenyl)-N-methylformimidamide;
N'-(4-((4-(tert-butyl)phenyl)(methyl)amino)-5-fluoi -2-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(methyl(m olyl)amino)phenyl)-N-methylformimidamide;
N-ethyl-N'-(7-((2-methoxyphenyl)amino)-2,3-dihydro- l H-inden-4-yl)-N-methylformimidamide; N-ethyl-N-methyl-N'-(7-(p-tolylamino)-2,3-dihydro- l H-inden-4-yl)formimidamide;
N'-(7-((4-chlorophenyl)amino)-2,3-dihydro-l H-inden-4-yl)-N-etliy]-N-methylformimidamide;
N-ethyl-N-methyl-N'-(4-(phenylamino)naphthalen-l -yl)formimidamide;
N'-(2,5-dimethyl-4-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide and N'-(2-c]iloro-5-methyl-4-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide;
* 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 ordinary 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, iso-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.
"cycloalkyl" or "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. cycloalkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. cycloalkynyl, similarly refers to cyclic pentynyl, hexynyl, heptynyl and octynyl.
"cycloalkyloxy" includes, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy.
"cycloalkylthio" includes, for example, cyclopropylthio, cyclobutylthio, cyclopentylthio.
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 "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 aiyl 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 "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 "heterocycle" 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 "heterocycle" 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-isoxazolyI; 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-imidazolyI; 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; l -pyrazolyl; 1 ,2,4-triazoI-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; 1,2,4, 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-yI; indoI-5-yl; indol-6-yl; indoI-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-yI; 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; 1,3-benzoxazol- 2- yl; l,3-benzoxazol-4-yl; l,3-benzoxazol-5-yI; l ,3-benzoxazol-6-yl; l,3-benzoxazol-7-yl and the liked. Non-limiting examples of benzofused 6-membered heteroaryl include quinolin-2-yl; quinolin-3-yl; quinolin-4-yl; quinolin-5-yl; quinolin-6-yI; quinolin-7-yl; quinolin-8-yl; isoquinolin-l-yl; isoquinolin- 3- yl; isoquinolin-4-yl; isoquinolin-5-yl; isoquinolin-6-yl; isoquinolin-7-yl; isoquinolin-8-yl and the like.
The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoroethyl, 2-
fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1 ,l -dichloro-2,2,2-trifluoroethyl, and 1 ,1 , 1 -trifluoroprop-2-yl .
The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio" are defined analogously except that, instead of alkyl groups, aikenyl, alkynyl, alkoxy and alkylthio groups are present as a part of the substituent.
The total number of carbon atoms in a substituent group is indicated by the"Ci-j" prefix where i and j are numbers from 1 to 21. For example, Cr3 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 (1) 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.
2.0
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, insect, 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, Chyt.ridiomycet.es, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycel.es.
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, Enterobacteriaceae, 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 (I) can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling
2.1
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 (1) 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 alkylaryl 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/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 arc cmulsifiers 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, aikylsulphonates, 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.akmwood.net/pesticides). Others are described by their systematic name following the lUPAC 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
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, (Al l ) dodemorph acetate, (A 12) epoxiconazole, (A 13) etaconazole, (A14) fenarimol, (A 15) 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-(lH-l ,2,4-triazol-l -yl)cyclofieptanol, (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-(trimethylsilyI)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}-l H-l,2,4-triazol-5-yl thiocyanate, (A68) 5-(allylsulfanyl)-l-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-l H-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]methyl}-2,4-dihydro-3H- l ,2,4-triazole-3-thione, (A71 ) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difli)orophenyl)oxiran-2-y]]methyl}-2,4-dihydro-3H-l ,2,4 riazole-3 hione, (A72) 1 - { [rel(2R,3 S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-y l]methyl } - 1 H- 1 ,2,4-triazol-5-yl thiocyanate, (A73) 1 -{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-l H-l ,2,4-triazo]-5-yl thiocyanate, (A74) 5-(allylsulfanyl)-l-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazole, (A75) 5-(allylsulfanyl)-l -{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methyl}-lH- 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- 1 ,2,4-triazole-3-thione, (A77) 2-[(2R,4S,5 S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- l ,2,4-triazole-3-thione, (A78) 2-[(2R,4R,5R)-l-(2,4-dichlorophenyI)-5-hydroxy-2,6,6-trimethyIheptan-4-yl]-2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A79) 2-[(2S,4R,5R)- 1 -(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-trimethylheptan-4-yl]-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A81 ) 2-[(2R,4S,5R)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-l ,2,4-triazole-3-thione, (A83) 2-[(2S,4R,5S)-l -(2,4-dichIorophenyI)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydi -3H- l ,2,4-triazole-3-thione, (A84) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl')phenyl]-l -(l H-l ,2,4-triazol-l -yl)propan-2-ol, (A85) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A86) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l -(lH-l ,2,4-triazol-l -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 -( l H-l ,2,4-triazol-l -yl)pi pan-2-ol, (A89) (2R)-2-( l -chlorocyclopropyl)-4- [( 1 R)-2,2-dichlorocyclopropyl]-l -( 1 H-l ,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-dichlorocyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 - yl)butan-2-ol, (A92) (2S)-2-(l -chlorocyclopropyl)-4-[(l R)-2,2-dichlorocyclopropyl]-l -( l H-l ,2,4-triazol-l -yl)biitan-2-ol, (A93) ( 1 S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl- 1 -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (A94) ( l R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l -(lH-1 ,2,4-triazol- 1 -y lmethyl)cyclopentanol, (A95) 5-(4-chlorobenzyl)-2- (chloromethyl)-2-methyl- 1 -( 1 H-l ,2,4-triazol-l-y]methyl)cyclopentanol.
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, (BI O) furametpyr, (B l l ) furmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1 RS,4SR,9SR), (B13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B 14) isopyrazam (anti-epimeric enantiomer 1 R,4S,9S), (B 15) isopyrazam (anti-epimeric enantiomer 1 S,4R,9R), (B16) isopyrazam (syn-epimeric racemate 1 RS,4SR,9RS), (B 17) isopyrazam (syn-epimeric enantiomer 1 R,4S,9R), (B 18) 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-(l , l ,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-fluoro-2-( 1 , 1, 2,3, 3,3-hexafluoropropoxy)phenyl]-l -methyl- 1H-pyrazole-4-carboxamide, (B29) N-[l-(2,4-dichlorophenyl)-l -methoxypropan-2-yl]-3- (difluoromethyl)-l -methyl- l H-pyrazole-4-carboxamide, (B30) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}pyhenyl)ethyl]quinazolin-4-amine, (B31 ) benzovindiflupyr, (B32) N-[(l S,4R)-9-(dichloromethylene)-l ,2,3,4-tetrahydro-l ,4-methanonaphthalen-5-yl]-3- (difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide, (B33) N-[(l R,4S)-9-(dichloromethylene)-l ,2,3,4-tetrahydro-l ,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-l -methyl-1 H-pyrazole-4-carboxamide, (B34) 3-(difluoromethyl)- 1 -methyl-N-( 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl)- 1 H-pyrazole-4-carboxamide, (B35) l ,3,5-trimethyl-N-( l , l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl)-lH-pyrazole-4-carboxamide, (B36) 1 -methyl-3-(trifluoromethyl)-N-( 1 , 1 ,3-trimethyl-2,3-dihydro-l H-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]-l H-pyrazole-4-carboxamide, (B38) l -methyl-3-(trifluoromethyl)-N-[(3S)-l , l ,3-trimethyl-2,3-dihydro-lH-inden-4-yl]- lH-pyrazole-4-carboxamide, (B39) 3- (difluoromethyl)-l -methyl-N-[(3S)-l , l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B40) 3-(difluoromethyl)- 1 -methyl-N-[(3R)- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-
yl]- 1 H-pyrazole-4-carboxamide, (B41 ) 1 ,3,5-trimethy 1-N-[(3R)- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden- 4- yl]-lH-pyrazole-4-carboxamide, (B42) l ,3,5-trimethyl-N-[(3S)- l , l ,3- trimethyl-2,3-dihydro-lH-inden-4-yl]-l H-pyrazole-4-carboxamide, (B43) benodanil, (B44) 2-chloro-N-( l , l ,3-trimethyI-2,3-dihydro-l H-inden-4-yl)pyridine-3-carboxamide, (B45) Isofetamid, (B46) l -methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyI)biphenyl-2-yl]- 1 H-pyrazole-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-l -methyl- l H-pyrazole-4-carboxamide, (B48) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-l -methyl- 1 H-pyrazole-4-carboxamide, (B49) 3-(difluoromethyl)-l -methyl -N-[4'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B50) N-(2',5 '-difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-l H-pyrazole-4-carboxamide, (B51 ) 3-(difluoromethyl)- l -methyl-N-[4'-(prop-l -yn-l-yl)biphenyl-2-yl]-l 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-l H-pyrazole-4-carboxamide, (B56) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)- l -methyl- 1 H-pyrazole-4-carboxamide, (B57) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-l ,3-dimethyl-lH-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- lH-pyrazole-4-carboxamide, (B62) 2-chloi -N-[4'-(3-hydiOxy-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-methylbut-l-yn- l -yl)biphenyl-2-yl]- l ,3-dimethyl-l H-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-( 1 ,1 ,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-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-l H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B69) 3-(difluoromethyl)-N-methoxy-l -methyl-N-[l -(2,4,6-trichlorophenyl)propan-2-yl]-l H-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-trimethyl-2,3-dihydro-lH-inden-4-yl]- 1 -methyl- 1 H-pyrazole-4-carboxamide, (B72) 3-(difluoromethy 1 )-N-[(3 S)-7-fluoro- 1 , 1 ,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l -methyl- l H-pyrazole-4-carboxamide.
Inhibitors of the respiratory chain at complex III, for example (C01 )
ametoctradin, (C02) amisulbrom, (C03) azoxystrobin, (C04) cyazofamid, (C05) coumethoxystrobin, (C06) coumoxystrobin, (C07) dimoxystrobin, (C08) enoxastrobin, (C09) famoxadone, (C I O)
fenamidone, (C l l ) fenaminstrobin, (C 12) flufenoxystrobin, (C13) fluoxastrobin, (C 14) kresoxim- methyl, (C 15) metominostrobin, (C16) mandestrobin, (CI 7) orysastrobin, (C18) 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- y]]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide, (C26) (2E)-2-(methoxyimino)-N-methyl-2-(2- {[({(lE)-l -[3-(trifluoromethyl)phenyl]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-pheny!vinyl]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, (C3 1 ) 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)-lFI-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.
D) Inhibitors of the mitosis and cell division, for example (D01 ) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) Albendazole, (D08) pencycuron, (D09) thiabendazole, (D10) thiophanate-methyl, (Dl l) thiophanate, (D12) zoxamide, (D13) 5-chloro-7-(4-methylpiperidin-l -yl)-6-(2,4,6 rifluorophenyl)[l,2,4]triazolo[l,5-a]pyrimi (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, (El O) dichlofluanid, (El l ) dithianon, (E12) dodine, (E13) dodine free base, (E14) ferbam, (El 5) fluorofolpet, (El 6) folpet, (E17) guazatine, (E l 8) guazatine acetate, (E19) 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, (E31) thiram, (E32) tolylfluanid, (E33) zineb, (E34) ziram, (E35) anilazine.
F) Compounds capable to induce a host defence, for example (FO I ) 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,(G10)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)-l -(morpholin-4-yl)prop-2-en-l -one.
J) Inhibitors of the lipid and membrane synthesis, for example (JOl ) biphenyl, (J02) chloroneb, (J03) dicloran, (J04) edifenphos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J10) propamocarb hydrochloride, (J 1 1 ) prothiocarb, (J12) pyrazophos, (J13) quintozene, (J 14) 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, (L10) metalaxyl-M (mefenoxam), (LI 1 ) ofurace, (LI 2) oxadixyl, (LI 3) oxolinic acid, (L14)octhilinone.
M) 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.
0) Further compounds, for example (O01 ) benthiazole, (O02) bethoxazin, (O03) capsimycin, (O04) carvone, (O05) chinomethionat, (O06) pyriofenone (chlazafenone), (O07) cufraneb, (O08)
cyflufenamid, (O09) cymoxanil, (Ol O) cyprosulfamide, (O i 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-oxazoI-3-yl]- l ,3 hiazoI-2-yl}piperidin- l ^^
pyrazol-l-yl]ethanone, (058) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,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]pyrimidin-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)-l H-pyrazol-l -yl]-l -(4-{4-[(5R)-5-phenyl-4,5-dihydro-l ,2-oxazoI-3-yl]-l ,3 hiazol-2-yl}piperidin- l -yl)ethanone, (065) 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l -yl] -(4-{4-[(5^
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-l H-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-difIuorophenyl)-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'-pbenyl-N'-(prop-2-yn-l -yl)thiophene-2-sulfonohydrazide, (077) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (078) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (079) 5-methyI-6-octyl[ 1 ,2,4]triazolo[ 1 ,5-a]pyrimidin-7-amine, (080) 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)methyl]-2,4-dichloronicotinamide, (085) N-[ l-(5-broino-3-chloropyridin-2-y!)ethyl]-2,4-dichloronicotiiiairiide, (086) N-[l -(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (087) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]metliyl}-2-plieny]acetaiT)ide, (088) N-{(Z)-[(cyclopropy]methoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl] methyl} -2-phenylacetamide, (089) N'-{4-[(3-tert-buty]-4-cyano-l ,2-thiazol-5-yl)oxy]-2-chloro-5-methylpheny]}-N-ethyl-N-methylimidoformamide, (O90) N-methyl-2-(l-{[5-methyl-3-(trifluoi methyl)-l H-pyrazol-l -yl]acety]}piperidin-4-yl)-N-( l ,2,3,4 etrahydronaphthalen-l-yl)-l ,3 hiazole-4-carboxamide, (091 ) N-methyl-2-( 1 -{ [5-methyl-3-(trifluoromethyl)- 1 H-pyrazol- 1 -yl]acetyl}piperidin-4-yl)-N-[( l R)-l ,2,3,4-tetrahydronaphthalen-l -yl]-l ,3-thiazole-4-carboxamide, (092) N-methyl-2-(l -{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N-[( I S)- 1 ,2,3,4- tetrahydronaphthalen-l -yl]-l ,3-thiazolc-4-carboxamide, (093) pentyl {6-[({[(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl} carbamate, (094) phenazine-l -carboxylic acid, (095) quinolin-8-ol, (096) quinolin-8-ol sulfate (2: 1), (097) teit-butyl {6-[({[(l -methyl- 1 H-tetrazol-5-yl)(phenyl) methylene]amino}oxy)methyl]pyridin-2-yl} carbamate, (098) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl) methanone, (099) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-l -yl]oxy}-3-methoxyphenyl)thyl]-N2-(methylsulfonyl)valinamide, (0100) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (O101) but-3-yn-l-yl {6-[({[(Z)-(l -methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl} carbamate, (0102) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(l H)-one), (O103) propyl 3,4,5-trihydroxybenzoate, (0104) [3-(4-chloiO-2-fluorophenyl)-5-(2,4-difluorophenyl)-l ,2-oxazol-4-yl](pyridin-3-yl)methanol, (0105) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l ,2-oxazol-4-yl](pyridin-3-yl)methanol, (0106) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l ,2-oxazol-4-yl](pyridin-3-yl)methanol, (0107) 2-fluoro-6-(trifluoromethyl)-N-( l ,l ,3-trimethyl-2,3-dihydro-l H-inden-4-yl)benzamide, (0108) 2-(6-benzylpyridin-2-yl)quinazoline, (0109) 2-[6-(3-fliioro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (01 10) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l -yl)quinoline, (01 1 1 ) Abscisic acid, (01 12) N'-[5-bromo-6-(2,3-dihydro-l H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (01 13) N'-{5-bromo-6-[l -(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (01 14) N'-{5-bromo-6-[( l R)-l -(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (01 15) N'-{5-biOmo-6-[(l S)- l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (01 16) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy] -2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (01 17) N'-{5-bromo-6-[(trans-4-isopiOpylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (Ol 1 8) N-cyclopropyl-3-(difluoi methyl)-5-fluoro-N-(2-isopropylbenzyl)-] -methyl- 1 H-pyrazole-4-carboxamide, (01 19) N-cyclopi pyl-N-(2-cyclopropylbenzyl)-3-(difluoi methyl)-5-fluoro-l -methyl-
1 H-pyrazole-4-carboxamide, (0120) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro- 1 -methyl- 1 H-pyrazole-4-carboxamide, (0121 ) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3 -(difluoromethyl)-5-fluoiO-l -methyl-l H-pyrazole-4-carboxaniide, (0122) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoiO-l -methyl- l H-pyrazole-4-carboxamide, (0123) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l -methyl- lH-pyrazole- 4- carboxamide, (0124) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l -methyl-lH-pyrazole-4-carboxamide, (0125) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l -methyl- l H-pyrazole-4-carboxamide, (0126) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropy-3-(difluoromethyl)-5-fluoi -l -methyl- 1 H-pyrazole-4-carboxamide, (0127) N-cyclopropy]-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l -methyl- 1 H-pyrazole-4-carboxamide, (0128) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro- 1 -methyl- 1 H-pyrazolc-4-carboxamide, (0129) N-cyclopropyl-3-(difli)oromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-l -methyl- l H-pyrazole-4-carboxamide, (0130) N-cycIopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoi methyl)-5-fluoro-l -methyl- l H-pyrazole-4-carboxamide, (0131) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l -methyl-lH-pyrazole-4-carboxamide, (0132) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopi pyl-3-(difluoiOmethyl)-5-fluoro-l -methyl-lH-pyrazole-4-carboxamide, (0133) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-N-[5-methyl-2-(trifluoromethyl)beiizyl]-l H-pyrazole-4-carboxamide, (0134) N-[2-chloro-6-(trifluoiOmethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-iluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (0135) N-[3-chloro-2-fluoro-6- (trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoiOmethyl)-5-fliioiO-l -methyl- l H-pyrazole-4-carboxamide, (0136) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro- l -methyl-l H-pyrazole-4-carboxamide, (0137) N-cyclopiOpyl-3-(difliioromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l -methyl- lH-pyrazole-4-carbothioamide, (0138) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (0139) N'-{4-[(4,5-dichloro-l ,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (0140) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)- 1 ,3-dimethyl- 1 H-pyrazol-5-amine, (0141 ) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-l ,4-benzoxazepine, (0142) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (0143) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (0144) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-l ,3-dimethyl-l H-pyrazol-5-amine, (0145) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-l ,3-dimethyl-lH-pyrazol-5 -amine, (0146) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-l ,3-dimethyl-lH-pyrazol-5-amine, (0147) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5-amine, (0148) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-l ,3-dimethyl- 1 H-pyrazol-5 -amine, (0149) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)- 1 ,3-dimethyl- 1 H-pyrazol- 5- amine, (01 0) 4-(2-bromo-4-f uorophenyl)-N-(2-biOmo-6-fluoiOphenyl)-l ,3-dimethyl-l H-pyrazol- 5-amine, (0151) 4-(2-bromo-4-fluoiOphenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0152) N-(2-bi mophenyl)-4-(2-chIoro-4-fIuorop enyl)- 1 ,3-dimethyl- 1 H-pyrazol-5-amine, (0153) 4-(2-chloro-4-fluoi phenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0154) 4-(2-bromo-4- luorophenyl)-N-(2,6-difluoi phenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0155) 4-(2-bromo-4-fluoiOphenyl)-N-(2-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0156) N'-(4-{3- [(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (0157) N'-(2,5-dimethyl-4-{3 (l,l,2,2-tetrafluoi ethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (0158) N'-(2,5-dimethy]-4-{3-[(2,2,2-trifIuoroethyl)sulfanyl]phenoxy}p enyl)-N-ethyl-N-methylimidoformamide, (0159) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (0160) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}pheny])-N-ethyl-N-mcthylimidoformamide, (0161) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (0162) N'-(2,5-dimethyl-4-{[3-(l, 1,2,2-tetrafluoiOethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (0163) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,
(0164) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoiOpiOpoxy)pheny]]sulfanyl}phenyl)-N-ethyl-N-methyl imidoformamide, (0165) N'-(2,5-dimethyl-4-{[3-(pentafluoiOethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidofomiamide, (0166) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2-yn- 1 -y loxy)phenyl]-4,5 -dihydro- 1 ,2-oxazol-3 -yl } - 1 ,3-thiazol-2-yl)piperidin- 1 -yl]ethanone, (0167) 2-[3,5-bis(difluoiOmethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-fluoro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0168) 2-[3,5-bis(difluoromethyl)- 1 H-pyrazol- 1 -yl]- 1 -[4-(4- { 5 -[2-chloro-6-(prop-2-yn- 1 -yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0169) 2-{3-[2-(l-{[3,5-bis(difluoromethyl)-l H-pyrazol- l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro- 1,2-oxazol-5-yl}phenyl methanesulfonate, (O170) 2-{3-[2-(l-{[3,5-bis(diiluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl
methanesulfonate, (0171) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{(5S)-5-[2-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0172) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{(5R)-5-[2-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0173) 2-[3,5-bis(difluoromethyl)-l H-pyrazol- l-yl]-l-[4-(4-{(5S)-5-[2-fluoro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro- l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0174) 2-[3,5-bis(difluoromethyl)-1 H-pyrazol- l-yI]-l-[4-(4-{(5R)-5-[2-fluoro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazoI-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0175) 2-[3,5-bis(difluoromethyl)-l H-pyrazol- l-yl]-l-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, h(0176) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{(5R)-5-[2-
chloro-6-(prop-2-yn-l -yloxy)phenyl]-4,5-dihydro-l ,2-oxazol-3-yl}-l ,3 hiazol-2-y])piperidi yljethanone, (0177) 2-{(5S)-3-[2-( l -{[3,5-bis(difluoromethyl)-l H-pyrazol- l -yl]acetyl} piperidin-4-yl)-l ,3-thiazol-4-yl]-4,5-dihydro-l ,2-oxazol-5-yl}phenyl methanesulfonate, (0178) 2-{(5R)-3-[2-( l -{ [3, 5-bis(difluoromethyl)- l H-pyrazol- l -yl]acetyl}pipe^^
oxazol-5-yl}phenyl methanesulfonate, (0179) 2-{(5S)-3-[2-(l -{[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-y])- l ,3-thiazol-4-yl]-4,5-dihydiO-l ,2-oxazol-5-yl} -3-chlorophenyl methanesulfonate, (0180) 2- {(5R)-3 -[2-( 1 - { [3,5-bis(difluoromethyl)- 1 H-pyrazol- 1 -yl]acetyl}piperidin-4-yl)-] ,3-thiazol-4-yl]-4,5-dihydro-l ,2-oxazol-5-yl} -3-chlorophenyl
methanesulfonate, (0181 ) (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypicolinamido} -6-methyl-4,9-dioxo-l ,5-dioxonan-7-yl isobutyrate.
As described above the compound of formula (I) can be mixed with one or more active compatible compound selected from insecticides/acaricides/nematicides class. The active ingredients from the classes of insecticides/acaricides/ nematicides 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.alanwood.net/pesticides).
( 1 ) Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.
(2) GABA-gated chloride channel antagonists, such as cyclodiene organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.
(3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [( lR)-/ra«i-isomers], deltamethrin, empenthrin [(EZ)-( l R)-isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [( l R)-/ra«, '-isomer), prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofeii, tefluthrin, tetramethrin, tetramethrin [( l R)-isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids, for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, for example spinetoram and spinosad.
(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.
(7) Juvenile hormone mimics such as juvenile hormone analogues, for example hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides for . example as methyl bromide and other alkyl halides or chloropicrin or fluorides or borates or tartar emetic or methyl isocyanate generators.
(9) Chordotonal organ TRPV channel modulators such as pyridine azomethine derivatives, for example pymetrozine and pyrifluquinazon or flonicamid.
( 10) Mite growth inhibitors, for example clofentezine, hexythiazox and diflovidazin or etoxazole.
( 1 1 ) Microbial disruptors of insect gut midgut, for example Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and Bacillus sphaericus and BT crop proteins: Cryl Ab, Cry 1 Ac, Cry 1 Fa, CrylA 105, Cry2Ab, Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab l / Cry35Abl .
(12) Inhibitors of mitochondrial ATP synthase such as organotin miticides, for example azocyclotin, cyhexatin and fenbutatin oxide or diafenthiuron or propargite or tetradifon.
( 13) Uncouplers of oxidative phosphorylation acting via disruption of the proton gradient, for example chlorfenapyr, DNOC and sulfluramid.
(14) Nicotinic acetylcholine receptor (nAChR) channel blockers, such as bensultap, cartap-hydrochloride, thiocyclam and thiosultap-sodium.
(15) Inhibitors of chitin biosynthesis, type 0, such as bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitors of chitin biosynthesis, type 1 , such as buprofezin.
(17) Molting disrupters (particularly in Dipteran), such as cyromazine.
(18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Octopamine receptor agonists, such as amitraz.
(20) Mitochondrial complex III electron transport inhibitors such as hydramethylnon or acequinocyl or fluacrypyrim or bifenazate.
(21 ) Mitochondrial complex I electron transport inhibitors, for example, MET1 acaricides and insecticides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
(22) Voltage-dependent sodium channel blockers such as indoxacarb or metaflumizone.
(23) Inhibitors of acetyl CoA carboxylase, such as tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.
(24) Mitochondrial complex IV electron transport inhibitors, such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphine or cyanides.
(25) Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, for example cyenopyrafen and cyflumetofen or carboxanilides.
(28) Ryanodine receptor modulators such as diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide.
(29) Chordotonal organ modulators on undefined target site such as flonicamid.
Further active ingredients with unknown or indeterminate mode of action, such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, diflovidazin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, triflumezopyrim and iodomethane; furthermore, preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following known active compounds: 1 -{2-fluoro-4-methyl-5-[(2,2,2-trifluoi ethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-lH-l ,2,4-triazol-5-amine (known from
WO2006043635), { l '-[(2E)-3-(4-chlorophenyl)prop-2-ene-l -yl]-5-fluorospiro[indole-3,4'-piperidine]-l (2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003106457), 2-chloro-N-[2-{ l -[(2E)-3-(4-chlorophenyl)prop-2-en- l-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006003494), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-l ,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l ,8-diazaspiro[4.5]dec-3-en-4-yl ethylcarbonate (known from WO2009049851), 4-(but-2-in-l -yIoxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluoropyrimidine (known from WO2004099160), 4-(but-2-in-l -yloxy)-6-(3-chloropheny pyrimidine (known from WO2003076415), PF1364 (CAS-Reg.No. 1204776-60-2), methyl-2-[2-({[3-bromo-l-(3-chloropyridin-2-yl)-l H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazincarboxylate (known from WO2005085216), methyl-2-[2-({[3-bromo-l -(3-chloropyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazincarboxylate (known from WO2005085216), methyl-2-[2-({ [3-bromo-l -(3-chloro-pyridin-2-yl)- l H-pyrazol-5-yl]carboiiyl}airiino)-5-cyano-3-methylbenzoyl]-2-methylhydrazincarboxylate (known from WO2005085216), methyl-2-[3,5-dibromo-2-({[3-bromo-l -(3-chloro-pyridin-2-yl)-l H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethyIhydrazincarboxylate
(known from WO2005085216), N-[2-(5-amino-l ,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-biOmo- l -(3-chloropyridin-2-yl)-l H-pyrazole-5-carboxamide (known from CN 102057925), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro- l ,2-oxazol-3-yl]-2HTiethyl-N-( l -oxidothietan-3-yl)benzamide (known from WO2009080250), N-[(2E)-l -[(6-chloropyridine-3-yl)methyl]pyridin-2(l H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012029672), l -[(2-chloro-l ,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[ 1 ,2-a]pyrimidin- 1 -ium-2-olate (known from WO2009099929), l -[(6-ch]oropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[ l ,2-a]pyrimidin- l -ium-2-olate (known from WO2009099929), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en- l -yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), N-[2-(/er/-butylcarbamoyl)-4-chloro-6-methylphenyl]-l-(3-chloropyridin-2-yl)-3-(fliioromethoxy)-lH-pyrazole-5-carboxamide
(known from WO2008134969), butyl-[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-l -en-l-yl]carbonate (disclosed in CN102060818), 3(E)-3-[l -[(6-chloro-3-pyridyl)methyl]-2-pyridyliden]-l ,l , l-trifluoropropan-2-one (known from WO2013144213), N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-l ,3-thiazol-5-yl]pyridine-2-carboxamide (known from WO2012000896), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-l -methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-lH-pyrazole-5-carboxamide (known from WO2010051926).
The compounds of formula (I) may be used to treat several fungal pathogens. Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include:
diseases caused by powdeiy mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucolricha; Sphaerotheca species, for example Sphaerotheca fuliginea Uncinula species, for example Uncinula necator; Erysiphe species, for example Erysiphe cichoracearu;
diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus;
diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lact cae; Peronospora species, for example Peronospora pisi or P. brassicae; Phyiophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum;
leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindeimithanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fljiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis;
root and stem diseases caused, for example, by Corticium species, for example Corticium gramineariim; Fusariwn species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; Ganoderma species, for example Ganoderma lucidum;
ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum;
diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda;
fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansion or Penicillium purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilhim species, for example Verticilium alboatrum;
seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, for example Penicillium expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii; Septoria species, for example Septoria nodorum; Typhula species, for example Typhula incarnata; Verticillium species, for example Verticillium dahliae;
cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galli gen a;
wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa;
deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans; Taphrina species, for example Taphrina deformans;
degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense;
diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea;
diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;
diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Psendomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora; Ralstonia species, for example Ralstonia solanacearum;
Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolind), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfect ), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivord), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as PoaceaelGramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
WE CLAIM
1 ) A compound of general formula (1)
(I)
wherein
R1 is selected from the group consisting of hydrogen, CN, SR", S(0)nR", OR", C,.12-alkyl, C1-]2-alkoxy, Ci.i2-alkylthio, C2.] 2-alkenyl, C2„i2-alkynyl, Ci.]2-haloalkyl, C2_] 2-haloalkenyl, C2„,2-haloalkynyl, C .8-cycloalkyl, Q-g-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].)2-alkyl, C2.i2-alkenyl, C2.i2-alkyny], Ci_]2-haloalkyl, C2.12-haloalkenyl, C2.12-haloalkynyl, C _8-cycloalkyl, C4_8-cycloalkenyl, C5„8-cycloalkynyl, C5.i8-ary], 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)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)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 all of the groups 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,.l2-alkyl, C2.,2-alkenyl, C2.,2-alkynyl, CM 2-haloalkyl, C2.i2-haloalkenyl, C2.]2-haloalkynyl, Q.^-haloalkoxy, Ci.] 2-haloalkylthio, C .8-cycloalkyl, C4_8-cycloalkenyl, C5.8-cycloalkynyl, C3.8-cycloalkyloxy, C3.8-cycloalkylfhio, C5.18-aryl, C7_i9-aralkyl, C7.i 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 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 all of the groups of 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 is selected from the group consisting of hydrogen, CN, SCN, S(0)nR", SiR'3, NR'R", (C=0)-R", CR -NR", Ci_]2-alkyl, C2_ i2-alkenyl, C2.12-alkynyl, Ci„i2-haloalkyl, C2.]2-haloalkenyl, C2.]2-haloalkynyl, C3_s-cycloalkyl, C4.8-cycloalkenyl, C5.8-cycloalkynyl, C5.i8-aryl, C7.i9-aralkyl, C7.i9-alkaryl, heterocyclyl, C3„8-heterocyclylalkyl; 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'2s SiR'3, COOR', CN, and CONR'2; or wherein
A is selected from the group consisting of fused or non-fused Q_i8-aryl, C5_i 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 R9; wherein
R9 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", OSiR'3, NR'S(0)nR", Ci.g-alkyl-S(0)„R", C,.g-alkyl-(C=0)-R", CR'=NR", S(0),1C5.18-aryl, S(0)nC7_19-aralkyl, S(0)nC7.19-alkaryl, C,.12-alkyl, C2-12-alkenyl, C2-12-alkynyl, Ci_]2-haloalkyl, C2.1 -haloalkenyl, C2.] 2-haloalkynyl, C] .i2-alkoxy, Ci_i2-alkylthio, Ci„i2-holoalkoxy, Ci_]2-haloalkylthio, C3.|2-cycloalkyl,C4.8-cycloalkenyl, C5_8-cycloalkynyl, C3_8-cycloalkyloxy, C3_8-cycloalkylthio, C7_) 9-aralkyl, C7_!9-alkaryl; bicyclic C5_i2-alkyl, C7.i2-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 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 four to
ten membered ring, which for its part may be substituted by one or more X, R', OR', SR', NR ¾ SiR'3, COOR', CN, and CONR'2;
and wherein all of the groups of R8 and R9 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;
wherein
R' represents hydrogen, straight chain or branched chain Ci_12.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].12-alkyl, C].]2-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.i8-aryl which is optionally substituted by one or more R';
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]_6-alkyl, Q^-alkoxy, Chalky lth io, Ci_6-haloalkyl, C3_s-cycloalkyl;
R2 and R3 are C| .6-alkyl, C2_6-alkenyl, C2.6- alkynyl, Ci.6-alkoxy, C^.alkylthio, Ci„6-haloalkyl, C3_8-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', NR'2, SiR'3, COOR', CN, and CONR'2;
R4 and R5 are of X, CN, S(0)nR", NR'R", (C=0)-R", CR'=NR", C,.6-alkyl, C2.6-alkenyl, C2_6-alkynyl, C|_6-haloalkyl, C].6-haloalky]thio, C3.8-cycloalky], C3.8-cycloalkylthio;
R6 and R7 are of hydrogen, X, CN, S(0)„R", NR'R", (C=0)-R", CR'=NR", C,.6-alkyl, C2.6-alkenyl, C2. 6-alkynyl, Ci.6-haloalkyl, C].6-haloalkylthio, C3.8-cycloalkyl, C .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;
R8 is hydrogen, CN, S(0)„R", NR'R", (C=0)-R", CR'=NR", C,_6-alkyl, C2-6-alkenyl, C2.6-alkynyl, Ci-6-haloalkyl, C3„8-cycloalkyl,C3.8-heterocyclyl, C3_8-heterocyclylalkyl;
R9 is X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)„R", OS(0)nR", OSiR'3, NR'S(0)„R", Ci.g-alkyl-S(0)„R", C,.6-alkyl-(C=0)-R", CR'=NR", C2.6-alkenyl, C2_6-alkynyl, C,.6-haloalkyl, C2_6-haloalkenyl, Q.^-alkoxy, C 1.12-alkylth.io, C].] 2-holoalkoxy, C1.] 2-haloalkylthio, C3.8-cycloalkyl,G- 4_8-cycloalkenyl, C3„8-cycloalkyloxy, C3.8-cycloalkylthio or two 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 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, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, iquinazolinyl, cinnonyl; substituted with one or more R9;
wherein R1 to R9 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 , 2 or 4 wherein the each substituent is independently selected from:
R1 is hydrogen or C],6-alkyl;
R2 and R3 are C^-alkyl, Ci.6-haloalkyl;
R4 and R5 are of X, CN, C,_6-alkyl, C,.6-haloalkyl, C3.8-cycloalkyl;
R6 and R7 are of hydrogen, X, Ci_6-alkyl, Ci.6-haloalkyl;
R8 is hydrogen, CN, S(0)nR", (C=0)-R", C,.6-alkyl, Ci.6-haloalkyl, C2.6-alkenyl, C2_6-alkynyl, C3.8-cycloalkyl, C3.6-heterocyclyl, C3.6-heterocyclylalkyl;
R9 is X, CN, SCN, SF5, R", OR", N02, NR"2, SiR'3, (C=0)-R", S(0)nR", C,.6-alkyl-S(0)nR", OS(0)nR", OSiR'3, NR'S(0)„R",
CR'=NR", SC].6-alkyl, C2.6-alkenyl, C2.6-alkynyl, C]_6-haloalkyl, C2_6-haloalkenyl, C]_i2-alkoxy, Ci_i2-alkylthio, C^n-holoalkoxy, C,.i2-haloalkylthio, C3_8-cycIoalkyl, C4.8-cycIoaIkenyI, C3.8-cycloalkyloxy, C3.8-cycloalkylthio or two 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)„, 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;
A is phenyl, napthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl isoxazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and quinolinyl; substituted with one or more R9;
wherein R1 to R9 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 -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'-(2,5-dimethyl-4-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(N-phenylmethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-methyl-4-(perfluoropropan-2-yl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3,4-dichlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidami N'-(2-chloro-5-methyl-4-(methyl(3,4,5-trifluorophenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3,4-dichlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-methoxyphenyl)(methyI)amino)-5-methylphenyl)-N-ethyI-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(4-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(p-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methy 1 form i m id am i d e ;
N'-(2-chloro-5-methyl-4-(N-phenylmethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-c loro-4-((4-chlorophenyl)(methyl)amino)-5-met ylphenyl)-N-ethyl-N-iTiethylforminii
N'-(2-chloro-4-((4-methoxyp enyl)(met yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((4-methoxy-3-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3,4-dimethoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((3,5-dimethoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((3-methoxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(p-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-methoxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((3-methoxypheny])amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(p-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(tert-butyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidam
N'-(4-((4-(tert-butyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-chlorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((2-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methy]formiinidamide;
N-ethyl-N'-(4-((2-fluorophenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluorophenyl)(methyl)amino)-2,5-dimethylpheny])-N-methylformimidamide;
N'-(2-chloro-4-((2-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidaniide;
N-ediyl-N'-(4-((3-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylfoririimidamide; N-ethyl-N'-(4-((4-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-((2-chlorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methy]formimidamide;
N-(4-(((ethyl(methyl)amino)methylene)amino)-2,5-dimethylphenyl)-N-phenylacetamide
N'-(2-chloro-5-methyl-4-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chlorophenyl)amino)-2,5-dimethy]phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-fluorophenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((2-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((3-fluoi phenyl)amino)-2,5-dimethylphenyl)-N-methy]formimidamide;
N'-(2-chloro-4-((2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-(3-chlorophenyl)-N,2,5-trimethyl-4-((morpholinomethylene)amino)aniline
N'-(2-chloro-4-((3-chloroplienyl)(mediyl)amino)-5-niethylphenyl)-N-ethyl-N-methylforminiidamide;
N-(3-Chlorophenyl)-N, 2, 5-trimethyl-4-((piperidin- l -ylmetIiylene) amino) aniline N-allyl-N'-(4-((3-ch]orophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(4-((3-chlorophenyi)(methyl)amino)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide; N'-(4-((2-bromop]ienyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-chlorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidam N'-(2,5-dimethyl-4-(methyl(2-(trifluoromethyl)phenyl)amino)p enyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidami N'-(2,5-dimethyl-4-((3-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimi
N'-(2,5-dimethyl-4-(methyl(4-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylfornn^nidamide
N-ethyl-N'-(4-((2-methoxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidami
N'-(2,5-dimethyl-4-(methyl(3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamid N'-(2-chloro-5-methyl-4-((3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-met oxypheny])amino)-5-metIiylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidaniide;
N'-(2-chloro-5-methyl-4-(methyl(o olyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-bromophenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidaraide;
N'-(4-((2-bromophenyl)(methy])amino)-2-ch]oro-5-methy]p]ienyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(methyl(o olyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methy]-4-((2-(trifluoromethyl)pheiiyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-(trifluoromet yl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-fluorophenyl)amino)-5-methylph
N'-(2-chloro-4-((4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-fliiorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylfonnimidami N'-(2-chloro-4-((4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-((3-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimi
N'-(2-chloro-5-methyl-4-((3-(trifluoi methyl)phenyl)amino)phenyl)-N-ethy]-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(3-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,6-difluorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2,6-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-((2,6-difluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimid N'-(2-chloro-4-((2,6-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-chloro-6-fluorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((2-chloro-6-fluorophenyl)amino)-5-methylphenyl)-N-ethy]-N-methylfonnimidamide; N'-(4-((2-chloro-6-fluorophenyl)(niethyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,6-dichloro-4-(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimida N'-(2-chloro-5-methyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((3-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methyl form i m i d am i d e ;
N'-(2,5-dimethyl-4-((4-(trifliioi methoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-((4-(trifliioromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-(trifluoiOmethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-5-methyl-4-(methyl(4-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(3-(trifluoiOmethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(N-phenylethylsulfonamido)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((2,4-dichloro-6-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N,-(2-chloi -4-((2-chloiO-6-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyI-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(4-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-ch]oro-5-methyl-4-(methyl(3-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((2-((trifluoromethyl)thio)phenyl)amino)pheny])-N-ethyl-N-methylformimidamide;
N'-(4-((3-((difluoiOmethyl)thio)pheny])amino)-2,5-dimethylphenyl)-N-ethy]-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-((trifluoromethy])thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(met yl(4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-((difluoromethyl)thio)phenyl)(methyl)amino)-2,5-dimethy]phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((3-((trifluoromeihyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(methyl(3-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N,-(2-chloro-5-methyl-4-(methyl(3-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-ch]oro-5-methyl-4-(methyl(4-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((3-(pentafluoro-16-sulfaneyl)pheny])amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-(pentafluoiO-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(3-(pentafluoro-16-sulfaneyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3,5-bis(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimid
N'-(4-((3,5-bis(trifluoromethyl)phenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-5-methyl-4-((3-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-(dimethylamino)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(dimethylamino)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidarnide; N'-(2-chloiO-4-((3-((difluoromethyl)thio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoromethoxy)phenyl)amino)-2,5-dimethylpheny])-N-ethyl-N-methylfoniiimidamide; N'-(4-((3-(difIuoromethoxy)phenyl)(methyl)amino)-2,5-dimethylpheiiyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((3-(difluoromethoxy)phenyl)amino)-5-methylpheny])-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-((2-(ti fluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((4-(difluoromethoxy)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-difluorophenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2,5-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-((3,5-bis(trif]uoi methyl)pheny])(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3,5-bis(trifluoromethyl)phenyl)(methyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((5-methyl-2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-difluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide
N'-(2-chloiO-4-((2,5-difluorophenyl)(methyl)amino)-5-methylplienyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(5-methyl-2-(trifluoromethyl)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chloiO-2-(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-chloro-2-(trifliioromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-chloro-2-(trifluoromethyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-chloro-2-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-(methyl(2-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((3-(difluoromethoxy)phenyl)(methyl)arnino)-5-iTiethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((2-(methylthio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-chloro-4-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-chloro-4-(ti fluoromethyl)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-chloiO-4-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((2-(metliy]thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-((4-fluoro-3-( l , l ,2,2-tetrafluoroethoxy)phenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-((4-fluoiO-3-( l , l ,2,2 etrafluoroethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
5-chloro-N-(2-fluorophenyl)-N,2-dimethyl-4-((morpholinomethylene)amino)aniline
N'-(2-chloi -4-(N-(2-fluorophenyl)methylsulfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-fluorophenyl)acetamide
N'-(2-chloro-4-((2-fluorophenyl)(methyl)amino)-5-methylphenyl)-N,N-dimethylformimidamide; N'-(2-chloro-4-(ethyl(2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; 5-chloro-N-(2-fluorophenyl)-N,2-dimethyl-4-((morpholinomethylene)amino)aniline
5-chloro-N-(2-fluorophenyl)-N,2-dimethyl-4-((thiomorpholinomethylene)amino)aniline
N-ethyl-N'-(5-fluoro-4-((4-fluoro-3-( l , l,2,2 etrafluoroethoxy)phenyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-4-((4-fluoro-3-(l , l ,2,2-tetrafluoroethoxy)phenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-chlorophenyl)acetamide;
N'-(2-chloro-4-(N-(2-chlorophenyl)methylsulfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-((difluoromethyl)thio)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-((difluoi methyl)tliio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-((difluoromethyl)thio)phenyl)(methyl)amino)-2,5-dimethylpheny])-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(ethyl(phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-pheny]acetamide; N'-(2-chloro-4-((2-((difluoromethyl)thio)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2-((difluoromethyl)thio)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(ethyl(3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((3-(difluoromethoxy)-4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-(N-(3-methoxyphenyl)methylsulfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoromethoxy)-4-fluoropheny])amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloiO-4-((3-(difluoromethoxy)-4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((3-(difluoi methoxy)-4-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2,5-dimethylphenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((2,5-dimethylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-ch]orophenyl)propionamide;
N-ethyl-N'-(5-fluoiO-4-((4-methoxypheny])amino)-2-methylphenyl)-N-methylformiinidamide; N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethy](methyl)amino)methylene)amino)-2-methylphenyl)-N-(2-fluorophenyl)propionamide
N'-(2-chloro-4-(N-(4-fluoro-3-( l , l ,2,2-tetrafluoroethoxy)phenyl)methy]siilfonamido)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-((3-( l , l ,2,2-tetrafluoroethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(3-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluoro-5-methylphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(5-fluoro-4-((2-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide;
N-ethyl-N'-(4-((2-fluoro-5-met ylplienyl)(methyl)amiiio)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(2-chloro-4-((2-fluoro-5-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(phenylamino)phenyl)-N-methylformimidamide;
N'-(4-((2-chlorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((4-(tert-bu1yl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidami
N-ethyl-N'-(5-fluoiO-2-methyl-4-(m-tolylamino)phenyl)-N-methylformimidamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyi)-N-phenylpropionamide;
N-(5-chloro-4-(((ethyl(methyl)amino)methylene)amino)-2-methylphenyl)-N-(3-methoxyphenyl)acetamide;
N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(4-((4-fluoiO-3-metlioxyphenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide;
N'-(4-((2-((difluoi methyl)thio)phenyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(4-((2-((difluoromethyl)thio)phenyl)(methyl)amino)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-6-fluoro-3-methyl-4-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloro-5-methyl-4-((5-oxo-5,6,7,8-tetrahydiOnaphthalen-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-bromo-6-fluoro-3-methyl-4-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylfonnimidamide; N'-(2-chloro-5-methyl-4-(( l -methylindolin-5-yl)amino)phenyl)-N-ethyl-N-methylfornn^nidamide; N'-(2,5-dimethyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(methyl(phenyl)amino)phenyl)-N-methylformimidamide;
N'-(4-((4-(tert-butyl)phenyl)(methyl)amino)-5-fluoiO-2-methylphenyl)-N-ethyl-N-methylformimidamide;
N-ethyl-N'-(5-fluoro-2-methyl-4-(methyl(m olyl)amino)phenyl)-N-methylformin^^amide;
N-ethyl-N'-(7-((2-methoxyphenyl)ann'no)-2,3-dihydro-l H-inden-4-yl)-N-methylfonnimidamide N-ethyl-N-methyl-N'-(7-(p-tolylamino)-2,3-dihydro-lH-inden-4-yl)formimidamide;
N'-(7-((4-chlorophenyl)amino)-2,3-dihydiO-l H-inden-4-yl)-N-ethyl-N-methylform
N-ethyl-N-methyl-N'-(4-(phenylamino)naphthalen-l -yl)formimidamide;
N'-(2,5-dimethyl-4-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2,5-dimethyl-4-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide;
N'-(2-chloi -5-methyl-4-(pyridin-2-ylamino)phenyl)-N-ethy]-N-methylformimidamide;
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 (1) 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 (1) 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 | 201917014768.pdf | 2019-04-12 |
| 2 | 201917014768-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [12-04-2019(online)].pdf | 2019-04-12 |
| 3 | 201917014768-STATEMENT OF UNDERTAKING (FORM 3) [12-04-2019(online)].pdf | 2019-04-12 |
| 4 | 201917014768-PRIORITY DOCUMENTS [12-04-2019(online)].pdf | 2019-04-12 |
| 5 | 201917014768-FORM 1 [12-04-2019(online)].pdf | 2019-04-12 |
| 6 | 201917014768-FIGURE OF ABSTRACT [12-04-2019(online)].pdf | 2019-04-12 |
| 7 | 201917014768-DECLARATION OF INVENTORSHIP (FORM 5) [12-04-2019(online)].pdf | 2019-04-12 |
| 8 | 201917014768-COMPLETE SPECIFICATION [12-04-2019(online)].pdf | 2019-04-12 |
| 9 | 201917014768-FORM-26 [08-07-2019(online)].pdf | 2019-07-08 |
| 10 | 201917014768-Power of Attorney-090719.pdf | 2019-07-13 |
| 11 | 201917014768-Correspondence-090719.pdf | 2019-07-13 |
| 12 | 201917014768-FORM 3 [27-01-2020(online)].pdf | 2020-01-27 |
| 13 | 201917014768-FORM 18 [23-09-2020(online)].pdf | 2020-09-23 |
| 14 | 201917014768-Proof of Right [16-06-2021(online)].pdf | 2021-06-16 |
| 15 | 201917014768-PETITION UNDER RULE 137 [16-06-2021(online)].pdf | 2021-06-16 |
| 16 | 201917014768-PETITION UNDER RULE 137 [16-06-2021(online)]-1.pdf | 2021-06-16 |
| 17 | 201917014768-OTHERS [16-06-2021(online)].pdf | 2021-06-16 |
| 18 | 201917014768-Information under section 8(2) [16-06-2021(online)].pdf | 2021-06-16 |
| 19 | 201917014768-FORM-26 [16-06-2021(online)].pdf | 2021-06-16 |
| 20 | 201917014768-FORM 3 [16-06-2021(online)].pdf | 2021-06-16 |
| 21 | 201917014768-FER_SER_REPLY [16-06-2021(online)].pdf | 2021-06-16 |
| 22 | 201917014768-CORRESPONDENCE [16-06-2021(online)].pdf | 2021-06-16 |
| 23 | 201917014768-COMPLETE SPECIFICATION [16-06-2021(online)].pdf | 2021-06-16 |
| 24 | 201917014768-CLAIMS [16-06-2021(online)].pdf | 2021-06-16 |
| 25 | 201917014768-ABSTRACT [16-06-2021(online)].pdf | 2021-06-16 |
| 26 | 201917014768-FER.pdf | 2021-10-18 |
| 27 | 201917014768-FORM 3 [11-01-2022(online)].pdf | 2022-01-11 |
| 28 | 201917014768-FORM 3 [02-08-2022(online)].pdf | 2022-08-02 |
| 29 | 201917014768-FORM 3 [22-12-2022(online)].pdf | 2022-12-22 |
| 30 | 201917014768-US(14)-HearingNotice-(HearingDate-25-07-2023).pdf | 2023-06-30 |
| 31 | 201917014768-FORM-26 [21-07-2023(online)].pdf | 2023-07-21 |
| 32 | 201917014768-Correspondence to notify the Controller [21-07-2023(online)].pdf | 2023-07-21 |
| 33 | 201917014768-Written submissions and relevant documents [09-08-2023(online)].pdf | 2023-08-09 |
| 34 | 201917014768-Written submissions and relevant documents [09-08-2023(online)]-1.pdf | 2023-08-09 |
| 35 | 201917014768-MARKED COPIES OF AMENDEMENTS [09-08-2023(online)].pdf | 2023-08-09 |
| 36 | 201917014768-FORM 13 [09-08-2023(online)].pdf | 2023-08-09 |
| 37 | 201917014768-AMMENDED DOCUMENTS [09-08-2023(online)].pdf | 2023-08-09 |
| 38 | 201917014768-Response to office action [12-01-2024(online)].pdf | 2024-01-12 |
| 39 | 201917014768-PatentCertificate12-01-2024.pdf | 2024-01-12 |
| 40 | 201917014768-IntimationOfGrant12-01-2024.pdf | 2024-01-12 |
| 1 | SearchstrategyE_22-12-2020.pdf |