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US 12,540,120 B2Granted
Herbicidal compounds
AssigneeSyngenta Crop Protection AG
InventorsKenneth Bruce Ling, Peter Timothy Seden, Christopher John Mathews, Stephen Edward Shanahan, Christiana Kitsiou, John Finney
Life of this patent
Estimating the term…
Abstract
The present invention relates to herbicidal substituted phenyl-pyridazine-diones and substituted phenyl-pyridazinone derivatives of formula (I), as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants.
Claims25
A compound of formula (I)
- or a salt or N-oxide thereof, wherein
- R1 is selected from the group consisting of C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkoxy, C1-C2alkoxy-C1-C2 alkyl, C2-C4alkenyl, C1-C4haloalkyl, cyano-C1-C4alkyl, C2-C4haloalkenyl, C2-C4alkynyl and C2-C4haloalkynyl;
- R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy-C1-C3alkyl-, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6 haloalkenyl, C2-C6alkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, —S(O)mC1-C6alkyl, amino, C1-C6alkylamino, C1-C6dialkylamino, —C(C1-C3alkyl)=N—O—C1-C3alkyl and C2-C6 haloalkynyl;
- G is hydrogen, or C(O)R3;
- R3 is selected from the group consisting of C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyl-S—, C1-C6alkoxy, —NR4R5 and phenyl optionally substituted by one or more R6;
- each R4 and R5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6alkoxy, and C3-C6cycloalkyl, or R4 and R5 together can form a morpholinyl ring;
- and,
- each R4a and R5a are independently selected from the group consisting of C1-C6alkoxy, and C3-C6cycloalkyl, or R4a and R5a together can form a morpholinyl ring;
- and,
- R6 is selected from the group consisting of halogen, cyano, nitro, C1-C3alkyl, C1-C3haloalky, C1-C3alkoxy and C1-C3haloalkoxy;
- X and Y are each independently hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3haloalkyl, C1-C3haloalkoxy, or halogen;
- D is a substituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, substituted on at least one ring carbon atom with R8 and/or on at least one ring nitrogen atom with R9;
- at least one R8 is selected from the group consisting of C1-C6haloalkylcarbonyl-, C3-C6cycloalkylcarbonyl-, —S(O)m—C1-C6haloalkyl, —S(O)m—C3-C6cycloalkyl, —O—S(O)2C1-C3alkyl, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, —NR4aR5a, —C(S)NR4R5, —S(O)2NHC(O)C1-C3alkyl, —S(O)2NR4R5, —C(O)OH, —C(O)OC1-C6alkyl, —C(O)NHS—(O)2C1-C6alkyl, —C(O)NR4R5, —NR4C(O)NR4R5, C1-C6alkylcarbonyl(C1-C6alkyl)amino-, C1-C6haloalkylcarbonylamino-, C1-C6haloalkylcarbonyl(C1-C6alkyl)amino-, C1-C6alkylsulfonylamino-, C1-C6alkylsulfonyl(C1-C6alkyl)amino-, C1-C6haloalkylsulfonylamino-, C1-C6haloalkylsulfonyl(C1-C6alkyl)amino-, C3-C6cycloalkylsulfonylamino-, C3-C6cycloalkylsulfonyl(C1-C6alkyl)amino-, hydroxyamino-, hydroxy(C1-C6alkyl)amino, C1-C6alkoxyamino, C1-C6alkoxy(C1-C6alkyl)amino, C1-C6haloalkoxyamino, C1-C6haloalkoxy(C1-C6alkyl)amino;
- and a ring system selected from the group consisting of a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16,
- at least one R9 is selected from the group consisting of C5-C6alkyl, C5-C6haloalkyl, C3-C6-cycloalkyl, C1-C3alkoxy-C3alkyl-, C3alkoxy-C1-C2alkyl-, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C1-C6hydroxyalkyl-, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, and a ring system selected from the group consisting of:
- a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- m is an integer of 0, 1, or 2;
- each R16 is independently halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- or D is a phenyl ring substituted by at least one R8;
- and,
- W is either
- wherein:
- “a” denotes the point of attachment to the phenyl-pyridazine dione/phenyl-pyridazinone moiety,
- “b” denotes the point of attachment to ring D,
- R10, R12, R14 and R15 are each independently hydrogen, C1-C3alkyl, or C1-C3haloalkyl;
- or R10 and R12 together with the carbon atoms to which they are joined forma a C3-C6 carbocyclic ring;
- and
- R11 and R13 are each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl;
- provided that when one of R11 or R13 is halogen, C1-C3alkyl or C1-C3haloalkyl, the other is hydrogen.
26 more elements
A compound of formula (I)
- or a salt or N-oxide thereof, wherein
- R1 is selected from the group consisting of C1-C4 alkyl, C3-C6cycloalkyl, C3-C6alkoxy, C1-C2 alkoxy-C1-C2alkyl, C2-C4alkenyl, C1-C4haloalkyl, cyano-C1-C4alkyl, C2-C4haloalkenyl, C2-C4alkynyl and C2-C4haloalkynyl;
- R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy-C1-C3alkyl-, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6 haloalkenyl, C2-C6alkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, —S(O)mC1-C6alkyl, —NR4R5, —C(C1-C3alkyl)=N—O—C1-C3alkyl and C2-C6 haloalkynyl;
- G is hydrogen, or C(O)R3;
- R3 is selected from the group consisting of C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyl-S—, C1-C6alkoxy, —NR4R5 and phenyl optionally substituted by one or more R6;
- each R4 and R5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6alkoxy, and C3-C6cycloalkyl, or R4 and R5 together can form a morpholinyl ring;
- and,
- R6 is selected from the group consisting of halogen, cyano, nitro, C1-C3alkyl, C1-C3haloalky, C1-C3alkoxy and C1-C3haloalkoxy;
- X is cyclopropyl;
- Y is hydrogen, C1-C3 alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3haloalkoxy, or halogen;
- D is a substituted or unsubstituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, and wherein when D is substituted it is substituted on at least one ring carbon atom with R8 and/or on a ring nitrogen atom with R9;
- each R8 is independently oxygen, hydroxyl, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6-cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6 haloalkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, C1-C6haloalkylcarbonyl-, C3-C6cycloalkylcarbonyl-, —S(O)m—C1-C6haloalkyl, —S(O)m—C3-C6cycloalkyl, —O—S(O)2C1-C3alkyl, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, —NR4R5, —C(S)NR4R5, —S(O)2NHC(O)C1-C3alkyl, —S(O)2NR4R5, —C(O)OH, —C(O)OC1-C6alkyl, —C(O)NHS—(O)2C1-C6alkyl, —C(O)NR4R5, —NR4C(O)NR4R5, C1-C6alkylcarbonyl(C1-C6alkyl)amino-, C1-C6haloalkylcarbonylamino-, C1-C6haloalkylcarbonyl(C1-C6alkyl)amino-, C1-C6alkylsulfonylamino-, C1-C6alkylsulfonyl(C1-C6alkyl)amino-, C1-C6haloalkylsulfonylamino-, C1-C6haloalkylsulfonyl(C1-C6alkyl)amino-, C3-C6cycloalkylsulfonylamino-, C3-C6cycloalkylsulfonyl(C1-C6alkyl)amino-, hydroxyamino-, hydroxy(C1-C6alkyl)amino, C1-C6alkoxyamino, C1-C6alkoxy(C1-C6alkyl)amino, C1-C6haloalkoxyamino, C1-C6haloalkoxy(C1-C6alkyl)amino;
- or a ring system selected from the group consisting:
- of a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- m is an integer of 0, 1, or 2;
- and
- each R9 is independently C1-C6alkyl, C1-C3haloalkyl, C3-C6-cycloalkyl, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C1-C6hydroxyalkyl-, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, or a ring system selected from the group consisting of:
- a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- each R16 is independently halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- or D is a substituted or unsubstituted phenyl ring, and wherein when said phenyl ring is substituted it is substituted by 1 to 5 R8;
- and,
- W is either
- wherein
- “a” denotes the point of attachment to the phenyl-pyridazine dione/phenyl-pyridazinone moiety,
- “b” denotes the point of attachment to ring D,
- R10, R12, R14 and R15 are each independently hydrogen, C1-C3alkyl, or C1-C3haloalkyl;
- or R10 and R12 together with the carbon atoms to which they are joined forma a C3-C6 carbocyclic ring;
- and
- R11 and R13 are each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl, provided that when one of R11 or R13 is halogen, C1-C3alkyl or C1-C3 haloalkyl, the other is hydrogen.
26 more elements
A compound of formula (I)
- or a salt or N-oxide thereof, wherein
- R1 is selected from the group consisting of C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkoxy, C1-C2alkoxy-C1-C2 alkyl, C2-C4alkenyl, C1-C4haloalkyl, cyano-C1-C4alkyl, C2-C4haloalkenyl, C2-C4alkynyl and C2-C4haloalkynyl;
- R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy-C1-C3alkyl-, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkyl, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6 haloalkenyl, C2-C6alkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, —S(O)mC1-C6alkyl, —NR4R5, —C(C1-C3alkyl)=N—O—C1-C3alkyl and C2-C6haloalkynyl;
- G is hydrogen, or C(O)R3;
- R3 is selected from the group consisting of C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyl-S—, C1-C6alkoxy, —NR4R5 and phenyl optionally substituted by one or more R6;
- each R4 and R5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6alkoxy, and C3-C6cycloalkyl, or R4 and R5 together can form a morpholinyl ring;
- and,
- R6 is selected from the group consisting of halogen, cyano, nitro, C1-C3alkyl, C1-C3haloalky, C1-C3alkoxy and C1-C3haloalkoxy;
- X is hydrogen, C1-C3alkyl, C1-C3alkoxy, C1-C3haloalkyl, C1-C3haloalkoxy, or halogen;
- Y is cyclopropyl;
- D is a substituted or unsubstituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, and wherein when D is substituted it is substituted on at least one ring carbon atom with R8 and/or on a ring nitrogen atom with R9;
- each R8 is independently oxygen, hydroxyl, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6-cycloalkyl, C1-C6alkoxy, C1-C3haloalkoxy, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, C1-C6haloalkylcarbonyl-, C3-C6cycloalkylcarbonyl-, —S(O)m—C1-C6haloalkyl, —S(O)m—C3-C6cycloalkyl, —O—S(O)2C1-C3alkyl, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl, —NR4R5, —C(S)NR4R5, —S(O)2NHC(O)C1-C3alkyl, —S(O)2NR4R5, —C(O)OH, —C(O)OC1-C6alkyl, —C(O)NHS—(O)2C1-C6alkyl, —C(O)NR4R5, —NR4C(O)NR4R5, C1-C6alkylcarbonyl(C1-C6alkyl)amino-, C1-C6haloalkylcarbonylamino-, C1-C6haloalkylcarbonyl(C1-C6alkyl)amino-, C1-C6alkylsulfonylamino-, C1-C6alkylsulfonyl(C1-C6alkyl)amino-, C1-C6haloalkylsulfonylamino-, C1-C6haloalkylsulfonyl(C1-C6alkyl)amino-, C3-C6cycloalkylsulfonylamino-, C3-C6cycloalkylsulfonyl(C1-C6alkyl)amino-, hydroxyamino-, hydroxy(C1-C6alkyl)amino, C1-C6alkoxyamino, C1-C6alkoxy(C1-C6alkyl)amino, C1-C6haloalkoxyamino, C1-C6haloalkoxy(C1-C6alkyl)amino;
- or a ring system selected from the group consisting:
- of a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- m is an integer of 0, 1, or 2;
- and
- each R9 is independently C1-C6alkyl, C1-C6haloalkyl, C3-C6-cycloalkyl, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C1-C6hydroxyalkyl-, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, or a ring system selected from the group consisting of:
- a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- each R16 is independently halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- or D is a substituted or unsubstituted phenyl ring, and wherein when said phenyl ring is substituted it is substituted by 1 to 5 R8;
- and,
- W is either
- wherein
- “a” denotes the point of attachment to the phenyl-pyridazine dione/phenyl-pyridazinone moiety,
- “b” denotes the point of attachment to ring D,
- R10, R12, R14 and R15 are each independently hydrogen, C1-C3alkyl, or C1-C3haloalkyl;
- or R10 and R12 together with the carbon atoms to which they are joined forma a C3-C6 carbocyclic ring;
- and
- R11 and R13 are each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl, provided that when one of R11 or R13 is halogen, C1-C3alkyl or C1-C3 haloalkyl, the other is hydrogen.
26 more elements
A compound of Formula (I),
- as defined in the below table
- #
- R1
- R2
- G
- X
- Y
- W
- D
- 1
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-oxazol-5-ylphenyl-
- 2
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-acetamidophenyl-
- 3
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(dimethylsulfamoyl)phenyl-
- 4
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-tert-butylphenyl-
- 5
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-biphenyl-
- 6
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl-
- 7
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 2-cyanophenyl-
- 8
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 3-cyanophenyl-
- 9
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-amino-3-methylphenyl-
- 10
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-methylsulfonylphenyl-
- 11
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-dimethylaminophenyl-
- 12
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-methylaminophenyl-
- 13
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-tert-butoxyphenyl-
- 14
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-cyanophenyl-
- 15
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-hydroxyphenyl-
- 16
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-cyclopropylphenyl-
- 17
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(methylsulfanyl)phenyl-
- 18
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-carboxyphenyl-
- 19
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-methoxycarbonylphenyl-
- 20
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(tert-butoxycarbonylamino)-3-fluoro-phenyl-
- 21
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 2-(methylsulfanyl)-4-pyridyl-
- 22
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 2-acetamido-4-pyridyl-
- 23
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- (E) —CH═CH—
- 4-biphenyl-
- 24
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- (E) —CH═CH—
- 3-cyanophenyl-
- 25
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- (E) —CH═CH—
- 4-hydroxyphenyl-
- 26
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl-
- 27
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 2-cyanophenyl-
- 28
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 3-cyanophenyl-
- 29
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-tert-butoxyphenyl-
- 30
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-cyanophenyl-
- 31
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-cyclopropylphenyl-
- 32
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- (E) —CH═CH—
- 2-cyanophenyl-
- 33
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- (E) —CH═CH—
- 3-cyanophenyl-
- 34
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- (E) —CH═CH—
- 4-tert-butoxyphenyl-
- 35
- —Me
- —Me
- —(C═O)iPr
- 6-F
- 3-Cl
- (E) —CH═CH—
- 4-cyanophenyl-
- 36
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(1-methylpyrazol-3-yl)phenyl-
- 37
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(5-methyltetrazol-1-yl)phenyl-
- 38
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-morpholinophenyl-
- 39
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(3-methylpyrazol-1-yl)phenyl-
- 40
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(3,5-dimethylpyrazol-1-yl)phenyl-
- 41
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-pyrazol-1-ylphenyl-
- 42
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-pyrrol-1-ylphenyl-
- 43
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(5-methyltetrahydrofuran-2-yl)phenyl-
- 44
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(5-methyl-2-furyl)phenyl-
- 45
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-oxazol-2-ylphenyl-
- 46
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(2-methylthiazol-4-yl)phenyl-
- 47
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(2-thienyl)phenyl-
- 48
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 1-phenyl-4-pyrazolyl-
- 49
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 1-cyclopropyl-4-pyrazolyl-
- 50
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(isopropylsulfanylmethyl)phenyl-
- 51
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-(methylsulfamoyl)phenyl-
- 52
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-sulfamoylphenyl-
- 53
- —Me
- —Me
- —H
- 6-F
- 3-Cl
- —CH2—CH2—
- 4-carbamoylphenyl-
430 more elements
A compound of formula (I)
- or a salt or N-oxide thereof, wherein
- R1 is selected from the group consisting of C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkoxy, C1-C2alkoxy-C1-C2 alkyl, C2-C4alkenyl, C1-C4haloalkyl, cyano-C1-C4alkyl, C2-C6haloalkenyl, C2-C6alkynyl and C2-C4haloalkynyl;
- R2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy-C1-C3alkyl-, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6 haloalkenyl, C2-C6alkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, —S(O)mC1-C6alkyl, amino, C1-C6alkylamino, C1-C6dialkylamino, —C(C1-C3alkyl)=N—O—C1-C3alkyl and C2-C6 haloalkynyl;
- G is hydrogen, or C(O)R3;
- R3 is selected from the group consisting of C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyl-S—, C1-C6alkoxy, —NR4R5 and phenyl optionally substituted by one or more R6;
- each R4 and R5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6alkoxy, and C3-C6cycloalkyl, or R4 and R5 together can form a morpholinyl ring;
- and,
- each R4a and R5a are independently selected from the group consisting of C1-C6alkoxy, and C3-C6cycloalkyl, or R4a and R5a together can form a morpholinyl ring;
- and,
- R6 is selected from the group consisting of halogen, cyano, nitro, C1-C3alkyl, C1-C3haloalky, C1-C3alkoxy and C1-C3haloalkoxy;
- X and Y are each independently hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3haloalkyl, C1-C3haloalkoxy, or halogen;
- D is a substituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, substituted on at least one ring carbon atom with R8 and/or on at least one ring nitrogen atom with R9;
- at least one R8 is selected from the group consisting of C1-C6haloalkylcarbonyl-, C3-C6cycloalkylcarbonyl-, —S(O)m—C1-C6haloalkyl, —S(O)m—C3-C6cycloalkyl, —O—S(O)2C1-C3alkyl, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, —NR4aR5a, —C(S)NR4R5, —S(O)2NHC(O)C1-C3alkyl, —S(O)2NR4R5, —C(O)OH, —C(O)OC1-C6alkyl, —C(O)NHS—(O)2C1-C6alkyl, —C(O)NR4R5, —NR4C(O)NR4R5, C1-C6alkylcarbonyl(C1-C6alkyl)amino-, C1-C6haloalkylcarbonylamino-, C1-C6haloalkylcarbonyl(C1-C6alkyl)amino-, C1-C6alkylsulfonylamino-, C1-C6alkylsulfonyl(C1-C6alkyl)amino-, C1-C6haloalkylsulfonylamino-, C1-C6haloalkylsulfonyl(C1-C6alkyl)amino-, C3-C6cycloalkylsulfonylamino-, C3-C6cycloalkylsulfonyl(C1-C6alkyl)amino-, hydroxyamino-, hydroxy(C1-C6alkyl)amino, C1-C6alkoxyamino, C1-C6alkoxy(C1-C6alkyl)amino, C1-C6haloalkoxyamino, C1-C6haloalkoxy(C1-C6alkyl)amino;
- and a ring system selected from the group consisting of a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- at least one R9 is selected from the group consisting of C5-C6alkyl, C5-C6haloalkyl, C3-C6-cycloalkyl, C1-C3alkoxy-C3alkyl-, C3alkoxy-C1-C2alkyl-, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C1-C6hydroxyalkyl-, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, and a ring system selected from the group consisting of:
- a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16;
- Any further R8 substituent may be selected from the group consisting of oxygen, hydroxyl, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6-cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C3alkoxy-C1-C3alkyl, C1-C3haloalkoxy-C1-C3alkyl-, C1-C3alkoxy-C1-C3alkoxy-C1-C3alkyl-, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6 haloalkynyl, C1-C6hydroxyalkyl-, C1-C6alkylcarbonyl-, C1-C6haloalkylcarbonyl-, C3-C6cycloalkylcarbonyl-, —S(O)m—C1-C6haloalkyl, —S(O)m—C3-C6cycloalkyl, —O—S(O)2C1-C3alkyl, —C1-C3alkyl-S(O)m—C1-C6alkyl, —C1-C3alkyl-S(O)m—C1-C6haloalkyl, —C1-C3alkyl-S(O)m—C3-C6cycloalkyl, cyano-C1-C6-alkyl-, NR4R5, —C(S)NR4R5, —S(O)2NHC(O)C1-C3alkyl, —S(O)2NR4R5, —C(O)OH, —C(O)OC1-C6alkyl, —C(O)NHS—(O)2C1-C6alkyl, —C(O)NR4R5, —NR4C(O)NR4R5, C1-C6alkylcarbonyl(C1-C6alkyl)amino-, C1-C6haloalkylcarbonylamino-, C1-C6haloalkylcarbonyl(C1-C6alkyl)amino-, —NR4C(O)NR4R5, C1-C6alkylsulfonylamino-, C1-C6alkylsulfonyl(C1-C6alkyl)amino-, C1-C6haloalkylsulfonylamino-, C1-C6haloalkylsulfonyl(C1-C6alkyl)amino-, C3-C6cycloalkylsulfonylamino-, C3-C6cycloalkylsulfonyl(C1-C6alkyl)amino-, hydroxyamino-, hydroxy(C1-C6alkyl)amino, C1-C6alkoxyamino, C1-C6alkoxy(C1-C6alkyl)amino, C1-C6haloalkoxyamino, C1-C6haloalkoxy(C1-C6alkyl)amino;
- or a ring system selected from the group consisting:
- of a phenyl ring, a 5-6-membered heteroaryl ring and a 3-6-membered heterocyclyl ring, wherein said ring system is substituted by 0 to 5 R16, wherein m, R4, R5 and R16 are as defined herein;
- m is an integer of 0, 1, or 2;
- each R16 is independently halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- or D is a phenyl ring substituted by at least one R8;
- and,
- W is either
- wherein:
- “a” denotes the point of attachment to the phenyl-pyridazine dione/phenyl-pyridazinone moiety,
- “b” denotes the point of attachment to ring D,
- R10, R12, R14 and R15 are each independently hydrogen, C1-C3alkyl, or C1-C3haloalkyl;
- or R10 and R12 together with the carbon atoms to which they are joined forma a C3-C6 carbocyclic ring;
- and
- R11 and R13 are each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl;
- provided that when one of R11 or R13 is halogen, C1-C3alkyl or C1-C3haloalkyl, the other is hydrogen.
29 more elements
Dependencies are inferred from the claim text.