# US 2023/0054449 A1 · Pyridazine (thio)amides as fungicidal compounds

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- Number: US 2023/0054449 A1
- Document ID: US20230054449A1
- Status: Published application
- Kind: A1
- Application number: 17/297,984
- Filed: 2019-11-27
- Published: 2023-02-23
- Earliest claimed: 2018-11-28
- Assignees: Bayer Aktiengesellschaft; Bayer CropScience AG
- Applicants: Bayer Aktiengesellschaft; Bayer CropScience AG
- Inventors: Victor CHEN; Pierre CRISTAU; Jérémy DUFOUR; Mazen ES-SAYED; Julie GEIST; Mathieu GOURGUES; Dominique LOQUE; Anthony MILLET; Daniel RACKL; Anne-Sophie REBSTOCK; Philippe RINOLFI; Yoshitaka SATO; Alexander SUDAU; Vincent THOMAS; Valérie TOQUIN
- Web page: https://patentgrep.com/patent/US20230054449A1

## CPC

- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01P 3/00: Fungicides
- C07D 237/24: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure relates to pyridazine (thio)amide compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.

## Claims

### Claim at position 1

1: A compound of formula (I):
wherein
T is O or S;
n is 0 or 1;
m is 0 or 1;
provided m is 1 when n is 1;
R1 is selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, —C(═O)Ra1, —C(═O)(ORa1), —S(═O)Ra1, —S(═O)2Ra1, —C(═O)N(Ra2)2 and S(═O)2N(Ra2)2, wherein Ra1 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, and C2-C6-alkenyl and Ra2 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C2-C6-alkenyl;
R2 and R3 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl and C3-C8-cycloalkyl, or R2 and R3 form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle;
R4 and R8 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl and C3-C8-cycloalkyl, or R4 and R5 form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle; or
R2 and R4 form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle, and R3 and R5 are independently hydrogen or halogen; or
R2 and R4 form together a covalent bond and R3 and R5 are independently hydrogen or C1-C6-alkyl;
R6 is selected from the group consisting of non-aromatic C3-C12-carbocycle, aromatic C6-C14-carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, non-aromatic C3-C12-carbocyclyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- to 14-membered heterocyclyloxy, non-aromatic 3- to 14-membered heterocyclyloxy, C1-C3-alkoxy substituted by a non-aromatic C3-C12-carbocycle, C1-C3-alkoxy substituted by an aromatic C6-C14-carbocycle, C1-C3-alkoxy substituted by a non-aromatic 3- to 14-membered heterocycle, C1-C3-alkoxy substituted by an aromatic 5- to 14-membered heterocycle, C1-C3-haloalkoxy substituted by a non-aromatic C3-C12-carbocycle, C1-C3-haloalkoxy substituted by an aromatic C6-C14-carbocycle, C1-C3-haloalkoxy substituted by a non-aromatic 3- to 14-membered heterocycle and C1-C3-haloalkoxy substituted by an aromatic 5- to 14-membered heterocycle, wherein cyclic, or cyclic moiety of, R6 substituents may be substituted with one or more R6S substituents that may be the same or different,
R6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkenyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, —N(Re)2, —C(═O)Rd, —C(═O)(ORd), —C(═O)N(Rd)2, —S(═O)2N(Rd)2, —O—Si(C1-C6-alkyl)3 and —Si(C1-C6-alkyl)3, or two R6S substituents may form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl,
wherein Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl and C3-C8-cycloalkyl,
wherein Rd is independently selected from the group consisting of hydrogen, C1-C6-alkyl and C1-C6-haloalkyl,
wherein aliphatic R6S, Rc and Rd substituents may be substituted with one or more substituents independently selected from the group consisting of cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein cyclic or cyclic moiety of R6S and cyclic Rc substituents may be substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl, and/or cyclic or cyclic moiety of R6S substituents may be substituted with two substituents forming, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl;
R7 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Re)2, —C(═NR)Rf, —NRgC(═O)Rg, —C(═O)(ORg), —C(═O)N(Rg)2, —S(═O)2N(Rg)2 and —S(═O)(═NRg)Rg,
wherein Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein Rf is independently selected from the group consisting of hydroxyl, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino and di(C1-C6-alkyl)amino,
wherein Rg is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,
wherein aliphatic R7, Re, Rf and Rg substituents may be substituted with one or more R7Sa substituents that may be the same or different,
wherein cyclic or cyclic moiety of R7, cyclic Re and cyclic Rg substituents may be substituted with one or more R7Sc substituents that may be the same or different,
R7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, aromatic C6-C14-carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
R7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle, or two R7Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl;
R8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, non-aromatic 3- to 14-membered heterocyclyloxy, aromatic 5- to 14-membered heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Rh)2, —SRi, —S(═O)Ri and —S(═O)2Ri,
wherein Rh is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein Ri is selected from the group consisting of C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein aliphatic Rg, Rh and Ri substituents may be substituted with one or more R8Sa substituents that may be the same or different,
wherein cyclic or cyclic moiety of Rg, cyclic Rh and cyclic Ri substituents may be substituted with one or more R8Sc substituents that may be the same or different,
R8Sa is selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, non-aromatic 3- to 7-membered monocyclic heterocycle and —N(Ra′)2 with Ra′ being independently selected from the group consisting of hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C1-C6-alkylcarbonyl, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle R8Sa may be substituted with one or more C1-C6-alkyl substituents that may be the same or different,
R8Sc is selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle that may be substituted with one or more C1-C6-alkyl substituents that may be the same or different, or two R8Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle may be substituted with one or more C1-C6-alkyl substituents that may be the same or different; and
Q is selected from the group consisting of aromatic C6-C14-carbocycle, non-aromatic C3-C12-carbocycle, non-aromatic 3- to 14-membered heterocycle and aromatic 5- to 14-membered heterocycle, wherein any of said carbocycle or heterocycle groups may be substituted with one or more Qs substituents that may be the same or different,
QS is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, non-aromatic 3- to 7-membered monocyclic heterocycle, aromatic 5- to 14-membered heterocycle, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —O—C(═O)Rj, —NRjC(═O)Rj, —C(═O)N(Rj)2, —C(═S)Rj, —C(═S)N(Rj)2, —C(═NRj)Rj, —C(═NORj)Rj and —N(Rk)2
wherein Rj is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy,
wherein Rk is independently selected from the group consisting of hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl and C3-C8-cycloalkyl,
wherein aliphatic QS, Rj and Rk substituents may be substituted with one or more substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein cyclic or cyclic moiety of Qs and cyclic Rk substituents may be substituted with one or more RQs substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and non-aromatic 3- to 7-membered monocyclic heterocycle, wherein cyclic RQs substituents may be substituted with two substituents forming, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl,
or a salt, N-oxide, or solvate thereof;
provided that the compound is not:
(a) 3-(1H-benzotriazol-1-yloxy)-N-(4-tert-butylphenyl)-6-chloropyridazine-4-carboxamide;
(b) 3-(cyclopentyloxy)-6-(4-fluorophenoxy)-N-{[(3R)-1-isopropylpiperidin-3-yl]methyl}pyridazine-4-carboxamide;
(c) 6-(4-fluorophenoxy)-N-{[(3R)-1-isopropylpiperidin-3-yl]methyl}-3-(tetrahydro-2H-pyran-4-yloxy)pyridazine-4-carboxamide;
(d) 6-chloro-N-{[(3R)-1-isopropylpiperidin-3-yl]methyl}-3-(tetrahydro-2H-pyran-4-yloxy)pyridazine-4-carboxamide;
(e) 6-chloro-3-(cyclopentyloxy)-N-{[(3R)-1-isopropylpiperidin-3-yl]methyl}pyridazine-4-carboxamide; or
(f) 3-(1H-benzotriazol-1-yloxy)-6-chloro-N-(cyclohexylmethyl)pyridazine-4-carboxamide.

### Claim at position 2 (depends on 1)

2: The compound of claim 1, wherein Q is selected from the group consisting of aromatic C6-C14-carbocycle, non-aromatic C7-C12 bicyclic system comprising an aryl fused to a C3-C8-cycloalkyl, non-aromatic C7-C12 bicyclic system comprising an aryl fused to a C3-C8-cycloalkenyl, non-aromatic 6- to 14-membered bicyclic heterocycle comprising a 4- to 6-membered monocyclic non-aromatic heterocycle fused to an aryl, non-aromatic 6- to 14-membered bicyclic heterocycle comprising a 5- or 6-membered monocyclic heteroaryl fused to a monocyclic C3-C8-cycloalkyl, aromatic 5- or 6-membered monocyclic heterocycle, aromatic 9- or 10-membered bicyclic heterocycle comprising an aromatic 5- or 6-membered monocyclic heterocycle fused to an aryl and 9- or 10-membered aromatic bicyclic heterocycle comprising two fused aromatic 5- or 6-membered monocyclic heterocycles, wherein each of said cyclic groups may be substituted with one or more Qs substituents that may be the same or different.

### Claim at position 3 (depends on 1)

3: The compound of claim 1, wherein Q is selected from the group consisting of phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl and indolyl, wherein said of phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl and indolyl may be substituted with one or more Qs substituents that may be the same or different.

### Claim at position 4 (depends on 1)

4: The compound of claim 1, wherein Qs is selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkyl, non-aromatic 3- to 7-membered monocyclic heterocycle and —N(Rk)2, wherein Rk is hydrogen.

### Claim at position 5 (depends on 1)

5: The compound of claim 1, wherein R6 is selected from the group consisting of aromatic C6-C14-carbocycle, non-aromatic polycyclic C7-C12-carbocycle, non-aromatic polycyclic 6- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, aromatic C6-C14-carbocyclyloxy, C1-C3-alkoxy substituted by an aromatic C6-C14-carbocycle and C1-C3-haloalkoxy substituted by an aromatic C6-C14-carbocycle, wherein cyclic, or cyclic moiety of, R6 substituents may be substituted with one or more R6S substituents that may be the same or different.

### Claim at position 6 (depends on 1)

6: The compound of claim 1, wherein R6 is selected from the group consisting of phenyl, indanyl, 1,2,3,4-tetrahydronaphthalenyl, spiro[cyclopropane-1,2′-indane]-1-yl, naphthyl, 2,3-dihydrobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, furanyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzofuranyl, benzoxazolyl, quinolinyl, isoquinolinyl, imidazo[1,2-a]pyridinyl, phenoxy, benzyloxy and —OCF2-phenyl, wherein cyclic, or cyclic moiety of, R6 substituents may be substituted with one or more R6S substituents that may be the same or different.

### Claim at position 7 (depends on 1)

7: The compound of claim 1, wherein R6S is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle, wherein cyclic R6S substituents may be substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxycarbonyl.

### Claim at position 8 (depends on 1)

8: The compound of claim 1, wherein Ri is selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl and —C(═O)(ORa1) with Ra1 being C1-C6-alkyl or C2-C6-alkenyl.

### Claim at position 9 (depends on 1)

9: The compound of claim 1, wherein R7 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C3-C8-cycloalkyl, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, —N(Re)2, —C(═NRf)Rf and —C(═O)N(Rg)2.

### Claim at position 10 (depends on 1)

10: The compound of claim 1, wherein R8 is selected from the group consisting of hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, aromatic C6-C14-carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, C3-C8-cycloalkyloxy, non-aromatic 3- to 14-membered heterocyclyloxy and —N(Rh)2.

### Claim at position 11 (depends on 1)

11: A composition comprising the compound of claim 1 and at least one agriculturally suitable auxiliary.

### Claim at position 12 (depends on 1)

12: A method for controlling phytopathogenic fungi comprising a step of applying at least one compound of claim 1 to a plant, a plant part, a seed, a fruit, or a soil in which a plant grows.

### Claim at position 13 (depends on 1)

13: A process for preparing a compound of formula (I) as recited in claim 1,
wherein R1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, —C(═O)Ra1, —C(═O)(ORa1), —S(═O)Ra1, —S(═O)2Ra1, —C(═O)N(Ra2)2 or S(═O)2N(Ra2)2, and T is O,
comprising a step of reacting a compound of formula (1)
wherein U1 is hydroxyl, halogen or C1-C6-alkoxy,
with an amine of formula (2)
wherein
R1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, —C(═O)Ra1, —C(═O)(ORa1), —S(═O)Ra1, —S(═O)2Ra1, —C(═O)N(Ra2)2 or S(═O)2N(Ra2)2.

### Claim at position 14 (depends on 1)

14: A process for preparing a compound of formula (I) as recited in claim 1,
wherein R1 is hydrogen, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, T is O, R8 is hydrogen or C1-C6-alkyl, R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2, comprising a step of reacting a compound of formula (3)
wherein G is halogen, R1 is hydrogen, hydroxyl, C1-C6-alkyl or C1-C6-alkoxy, R8 is hydrogen or C1-C6-alkyl, R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2, with a compound of formula (4)
in the presence of a base.

### Claim at position 15

15: A compound of formula (1):
wherein U1 is hydroxyl, halogen or C1-C6-alkoxy;
R7 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Re)2, —C(═NRf)Rf, —NRgC(═O)Rg, —C(═O)(ORg), —C(═O)N(Rg)2, —S(═O)2N(Rg)2 and —S(═O)(═NRg)Rg,
wherein each Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein each Rf is independently selected from the group consisting of hydroxyl, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino and di(C1-C6-alkyl)amino,
wherein each Rg is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,
wherein aliphatic R7, Re, Rf and Rg substituents may be substituted with one or more R7Sa substituents that may be the same or different,
wherein cyclic or cyclic moiety of R7, cyclic Re and cyclic Rg substituents may be substituted with one or more R7Sc substituents that may be the same or different,
R7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, aromatic C6-C14-carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle, R7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle, or two R7Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl:
R8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, aromatic C6-C14-carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, non-aromatic 3- to 14-membered heterocyclyloxy, aromatic 5- to 14-membered heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(Rh)2, —SRi, —S(═O)Ri and —S(═O)2Ri,
wherein each Rh is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein each Ri is selected from the group consisting of C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein aliphatic Rg, Rh and Ri substituents may be substituted with one or more R8Sa substituents that may be the same or different,
wherein cyclic or cyclic moiety of Rg, cyclic Rh and cyclic Ri substituents may be substituted with one or more R8Sc substituents that may be the same or different,
R8Sa is selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, non-aromatic 3- to 7-membered monocyclic heterocycle and —N(Ra′)2 with Ra′ being independently selected from the group consisting of hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C1-C6-alkylcarbonyl, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle R8Sa may be substituted with one or more C1-C6-alkyl substituents that may be the same or different,
R8Sc is selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle that may be substituted with one or more C1-C6-alkyl substituents that may be the same or different, or two R8Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle, wherein said non-aromatic 3- to 7-membered monocyclic heterocycle may be substituted with one or more C1-C6-alkyl substituents that may be the same or different:
Q is selected from the group consisting of aromatic C6-C14-carbocycle, non-aromatic C3-C12-carbocycle, non-aromatic 3- to 14-membered heterocycle and aromatic 5- to 14-membered heterocycle, wherein any of said carbocycle or heterocycle groups may be substituted with one or more QS substituents that may be the same or different,
QS is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, non-aromatic 3- to 7-membered monocyclic heterocycle, aromatic 5- to 14-membered heterocycle, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —O—C(═O)Rj, —NRC(═O)Rj, —C(═O)N(Rj)2, —C(═S)Rj, —C(═S)N(Rj)2, —C(═NRj)Rj, —C(═NORj)Rj and —N(Rk)2
wherein each Ri is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy,
wherein each Rj is independently selected from the group consisting of hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl and C3-C8-cycloalkyl,
wherein aliphatic QS, Rj and Rk substituents may be substituted with one or more substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein cyclic or cyclic moiety of QS and cyclic Rk substituents may be substituted with one or more RQs substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and non-aromatic 3- to 7-membered monocyclic heterocycle, wherein cyclic RQs substituents may be substituted with two substituents forming, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl; and
R7 and R8 are not simultaneously hydrogen, C1-C6-alkyl, or aromatic C6-C14-carbocycle,
provided that the compound is not:
methyl 6-chloro-3-(2,4-difluorophenoxy)pyridazine-4-carboxylate,
6-chloro-3-[(8-formyl-4-methyl-2-oxo-2H-chromen-7-yl)oxy]pyridazine-4-carboxylic acid,
6-chloro-3-[(3-formyl-7-methylquinolin-2-yl)oxy]pyridazine-4-carboxylic acid,
6-chloro-3-{[4-formyl-5-(hydroxymethyl)-2-methylpyridin-3-yl]oxy}pyridazine-4-carboxylic acid,
6-chloro-3-[(1-formyl-2-naphthyl)oxy]pyridazine-4-carboxylic acid,
6-chloro-3-(2-formyl-5-methoxyphenoxy)pyridazine-4-carboxylic acid, or
ethyl 3-phenoxy-6-phenylpyridazine-4-carboxylate.

### Claim at position 16

16: A compound of formula (3):
wherein
G is halogen;
n=1 and m=1;
R1 is hydrogen;
R2, R3, are hydrogen;
R4 and R5 are hydrogen or fluorine;
R6 is selected from the group consisting of non-aromatic polycyclic C7-C12-carbocycle, aromatic C6-C14-carbocycle, and non-aromatic 6- to 14-membered polycyclic heterocycle;
R7 is selected from the group consisting of hydrogen, halogen, hydroxyl, mercapto, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C3-C8-cycloalkyloxy, aromatic C6-C14-carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy and —N(Re)2,
wherein each Re is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C14-carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein aliphatic R7 and Re substituents may be substituted with one or more R7Sa substituents that may be the same or different,
wherein cyclic or cyclic moiety of R7 and cyclic Re substituents may be substituted with one or more R7Sc substituents that may be the same or different,
R7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, aromatic C6-C14-carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
R7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and non-aromatic 3- to 7-membered monocyclic heterocycle, or two R7Sc substituents form, together with the carbon atom to which they are attached to, a C3-C8-cycloalkyl; and
R8 is hydrogen or C1-C6-alkyl;
provided that the compound of formula (3) is not:
3,6-dichloro-N-[2-(3,5-difluorophenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(3-methylphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(3-chlorophenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(4-fluoro-2-methylphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(2-methylphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(4-hydroxyphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(3-fluorophenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(2-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(4-methoxyphenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(4-fluorophenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(2,4-dichlorophenyl)ethyl]pyridazine-4-carboxamide,
3,6-dichloro-N-[2-(2-fluorophenyl)ethyl]pyridazine-4-carboxamide, or
3,6-dichloro-N-(2-phenylethyl)pyridazine-4-carboxamide.