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ES2563461T3 - Agente de control de plagas - Google Patents

Agente de control de plagas Download PDF

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Publication number
ES2563461T3
ES2563461T3 ES13157997.1T ES13157997T ES2563461T3 ES 2563461 T3 ES2563461 T3 ES 2563461T3 ES 13157997 T ES13157997 T ES 13157997T ES 2563461 T3 ES2563461 T3 ES 2563461T3
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ES
Spain
Prior art keywords
ch2ch2
so2cf3
pyridyl
compound
sch3
Prior art date
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ES13157997.1T
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English (en)
Inventor
Shinzo Kagabu
Masaaki Mitomi
Shigeki Kitsuda
Ryo Horikoshi
Masahiro Nomura
Yasumichi Onozaki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Meiji Seika Pharma Co Ltd
Original Assignee
Meiji Seika Pharma Co Ltd
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Application filed by Meiji Seika Pharma Co Ltd filed Critical Meiji Seika Pharma Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • A—HUMAN NECESSITIES
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    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/98—Nitrogen atom
    • C—CHEMISTRY; METALLURGY
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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    • C07D213/72—Nitrogen atoms
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Abstract

Un derivado de amina, que es N-[1-((6-cloropiridin-3-il)metil)piridin-2(1H)-iliden]-2,2,2-trifluoroacetamida y exhibe un punto de fusion de 155 a 158 ºC en calorimetria diferencial de barrido (DSC) medido con una velocidad de aumento de temperatura de 10 ºC/min.

Description

imagen1
imagen2
imagen3
Tabla 1
Compuesto N.º
Ar R1 R2 R3 R4
1
(I) H CN CH2CH2 SCH3
2
(I) H CN CH2CH2 SCH2CH3
3
(I) H CN CH2CH2 SCH2CH2CH3
4
(I) H CN CH2CH2CH2 H
5
(I) H CN CH2CH2CH2 SCH3
6
(I) H CN CH2CH2 SCSSCH3
7
(I) H CN CH2CH2 SCSSCH2CH3
8
(I) H CN CH2CH2 SCSSCH2CH2CH3
9
(II) H CN CH2CH2 SCSSCH2CH3
10
(II) H CN CH2CH2 SCSSCH2CH2CH3
11
(I) H CN CH2CH2 OCH3
12
(I) H CN CH2CH2CH2CH2 H
13
(I) H CN CH2 H
14
(I) H CN CH2CH2 H
15
(I) H CN CH(CH3)CH2 H
16
(I) H CN CH2CH2 N(CH3)2
17
(I) H CN CH2 (I)
18
(I) Me CN CH2CH2 H
19
(II) H CN CH2CH2 H
20
(I) H COMe CH2CH2 H
21
(I) H COCF3 CH2CH2 H
22
(I) H COOMe CH2CH2 H
23
(II) H CN CH2CH2 SCH3
24
(I) H COMe CH2CH2 SCH3
25
(I) H COOPh CH2CH2 SCH3
26
(I) H SOOPh CH2CH2 SCH3
27
(I) H COOMe CH2CH2 SCH3
28
(I) H SOOMe CH2CH2 SCH3
29
(I) H CHO CH2CH2 SCH3
30
(I) H COPh CH2CH2 SCH3
31
(I) H COCF3 CH2CH2 SCH3
32
(II) H CN CH2CH2 SCH2CH3
33
(I) H PO(OC2H3)2 CH2CH2 SCH3 .
34
(I) H COCCl3 CH2CH2 SCH3
35
fenilo H CN CH2CH2 H
36
3-piridilo H CN CH2CH2 H
5
37
4-clorofenilo H CN CH2CH2 H
38
fenilo H CN CH2 fenilo
39
fenilo H COMe CH2CH2 H
40
fenilo H COOMe CH2CH2 H
41
3-tienilo H CN CH2CH2 H
42
(I) H CN CH2C≡C H
43
(I) H CN CH2CH=CH H
44
(I) H CN CH2 fenilo
45
3-cianofenilo H CN CH2CH2 H
46
6-trifluorometil-3-piridilo H CN CH2CH2 H
47
6-trifluorometil-3-piridilo H CN CH2CH2 SCH3
48
6-trifluorometil-3-piridilo H CN CH2CH2 SCH2CH3
49
(I) H CN CH2CH2 S-CH2-(2-furanilo)
50
(I) H CN CH2CH2 S-CH2-fenilo
51
(I) H CN CH2CH2 SOO-fenilo
52
(I) H CN CH2CH2 S-fenilo
53
(I) H CN CH2CH2 O-fenilo
54
(I) H CN CH2CH2 NHCOCH3
55
4-clorofenilo H CN CH2 4-clorofenilo
56
(I) H CN CH2 COOMe
57
(I) H CN CH2CH2 fenilo
58
(I) H CN CH2CH2 COO-fenilo
59
(I) H CN CH2 CN
60
(I) H CN CH(Me) CN
Tabla 2
Compuesto N.º
Ar R1 R2 R3 R4
61
(I) H CN CH2CH2 OCOMe
62
(I) H CN CH2 SCH3
63
(II) H CN CH2CH2 OCOMe
64
(II) H CN CH2 SCH3
65
(II) H CN CH2CH2 COOMe
66
(II) H CN CH2 ciclopropilo
67
(II) H CN CH (Me) CH SCH3
68
(I) H CN 2-tiiranileno H
69
(I) H CN 2-oxiranileno H
70
(I) H CN CH2CH2 COOMe
71
(I) H CN CH2 ciclopropilo
72
5,6-dicloro-3-piridilo H CN CH2CH2 SCH3
6
73
(I) Me CN CH2CH2 SCH3
74
(II) H CN CH2CH2 SCH3
75
(II) H CN CH2CH2 SCH2CH3
76
(I) H CN 3-tetrahidrotiofenileno H
77
(I) H CN CH (Me) CH SCH3
78
6-fluoro-3-piridilo H CN CH2CH2 SCH3
79
6-cloro-5-fluoro-3-piridilo H CN CH2CH2 SCH3
80
6-cloro-5-fluoro-3-piridilo H CN CH2CH2 H
81
(I) H COCF3 CH2CHF H
82
(I) H CN CH2CHF H
83
(I) H CN CH2 (II)
84
(I) H CN CH2CH2 OTs
85
(I) H CN CH2CH2 SCSN(Et)CH2Ph
86
(I) H CN CH2CH2 SCSOEt
87
(II) H CN CH2CH2 SCSOEt
88
(I) H CN CH2CH2 SCSN(Me)CH2Ph
89
(I) Me COCF3 CH2CHF H
90
(I) H CN CH2CH2 SCSOiPr
91
(I) H CN CH2CH2 SCSO-n-pentilo
92
(I) Me CN CH2CHF H
93
(I) H CN CH2CH2 SCSO-n-Pr
94
(I) H CN CH2CH2 SCSO-n-Bu
95
(II) H CN CH2CF2 H
96
(I) Me COCF3 CH2CF2 H
97
(I) H COCF3 CH2CF2 H
98
(I) H COCF2Cl CH2CF2 H
99
(I) H COCCl3 CH2CF2 H
100
(I) H CN CH2CH2CH2 OTs
101
(I) H CN CH2CH2CH2 SCSOEt
102
(I) H CN CH2CH2CH2 SCSO-n-Pr
103
(I) H CN CH2CH2CH2 SCSN (Et) CH2Ph
104
(I) H SO2CF3 CH2CF2 H
105
(I) Me COCF3 CH2CH2 H
106
(I) Me COCF3 CH2CH2CF2 H
107
(I) Me SO2CF3 CH2CH2 H
108
(I) Me SO2CF3 CH2CF2 H
109
(I) Et COCF3 CH2CF2 H
110
(I) Et SO2CF3 CH2CF2 H
7
111
(I) Et COCF3 CH2CH2 H
112
(I) Et SO2CF3 CH2CH2 H
113
(I) H CN CH2CH2 S-CH2-(2-imidazolilo)
114
6-trifluorometil-3-piridilo Me SO2CF3 CH2CH2 H
115
6-trifluorometil-3-piridilo Me COCF3 CH2CH2 H
116
(II) Me SO2CF3 CH2CH2 H
117
(II) Me SO2CF3 CH2CF2 H
118
(II) Et COCF3 CH2CF2 H
119
(II) H CN CH2CH=CH H
120
(II) H CN CH2C≡C H
Tabla 3
Compuesto N.º
Ar R1 R2 R3 R4
121
(II) H CN CH2 H
122
(II) H CN CH2CH2CH2 H
123
(II) Et SO2CF3 CH2CF2 H
124
2-piridilo Me SO2CF3 CH2CH2 H
125
(II) Et SO2CF3 CH2CF2 H
126
(II) Et COCF3 CH2CH2 H
127
(II) Et SO2CF3 CH2CH2 H
128
(I) H SO2CF3 CH2C≡C H
129
(I) H SO2CF3 CH2 CN
130
4-trifluorometil-3-piridilo H COCF3 CH2CH2 H
131
6-trifluorometil-3-piridilo H SO2CF3 CH2CH2 H
132
4-piridilo Me COCF3 CH2CH2 H
133
3-piridilo Me COCF3 CH2CH2 H
134
2-piridilo Me COCF3 CH2CH2 H
135
(I) H SO2CF3 CH2 H
136
(II) H CN CH2CH2 OTs
137
(II) H CN CH2CH2 SCSOEt
138
(II) H CN CH2CH2 SCSN (CH2Ph) Et
139
(I) H CN CH2CH2 S (=O) Ph
140
(I) H SO2CF3 CH2CH2CH2 H
141
(I) H SO2CF3 CH2CH2CH2CH2 H
142
(I) H SO2CF3 CH2CH2 SOOPh
143
(I) H SO2CF3 CH2CH2 OPh
144
(I) H SO2CF3 CH2CH2 H
145
(I) H SO2CF3 CH2CH2CH2 H
146
(I) H SO2CF3 CH2CH=CH H
8
147
(I) H SO2CF3 CH2 Ph
148
4-fluoro-3-piridilo H CN CH2CH2 H
149
4-bromo-3-piridilo H CN CH2CH2 H
150
(I) H SO2CF3 CH2CH2 NMe2
151
(I) Me SO2CF3 CH2CH2 NMe2
152
(I) H SO2CF3 CH2CH2C≡C H
153
3-cloro-4-piridilo H CN CH2CH2 H
154
3-cloro-2-piridilo H CN CH2CH2 H
155
(I) H SO2CF3 CH2CH2 OCH3
156
(II) H SO2CF3 CH2CH2 OCH3
157
6-cloro-3-piridazilo H COCF3 CH2CH2 H
158
3,5-diclorofenilo H CN CH2CH2 H
159
(I) H SO2CF3 CH2CH2 CN
160
(I) H SO2CF3 CH2 COOMe
161
(I) H SO2CF3 CN2 COOH
162
4-fluorofenilo H SO2CF3 CH2CH2 OCH3
163
(II) H SO2CF3 CH2 CN
164
4-metilfenilo H SO2CF3 CH2CH2 OCH3
165
6-trifluorometil-3-piridilo H SO2CF3 CH2 CN
166
2-piridilo H SO2CF3 CH2CH2 OCH3
167
6-cloro-5-fluoro-3-piridilo H SO2CF3 CH2 CN
168
3-piridilo H SO2CF3 CH2CH2 OCH3
169
4-piridilo H SO2CF3 CH2CH2 OCH3
170
(I) Me SO2CF3 CH2 CN
171
(I) Me SO2CF3 CH2C≡C H
172
(II) H SO2CF3 CH2C≡C H
173
6-fluoro-3-piridilo H SO2CF3 CH2CH2 OCH3
174
6-bromo-3-piridilo H SO2CF3 CH2CH2 OCH3
175
3,5-diclorofenilo Me COCF3 CH2CH2 H
176
3,5-diclorofenilo H COCF3 CH2CH2 H
177
fenilo H SO2CF3 CH2CH2 H
178
(I) H SO2CH2CF3 CH2CH2 H
179
(I) H SO2CH2CF3 CH2C≡C H
180
3-clorofenilo H SO2CF3 CH2CH2 H
Tabla 4
Compuesto N.º
Ar R1 R2 R3 R4
181
4-clorofenilo H SO2CF3 CH2CH2 H
182
3-cianofenilo H SO2CF3 CH2CH2 H
9
183
4-nitrofenilo H SO2CF3 CH2CH2 H
184
3,5-diclorofenilo H SO2CF3 CH2C≡C H
185
4-metilfenilo H SO2CF3 CH2CH2 H
186
4-cianofenilo H SO2CF3 CH2CH2 H
187
4-metoxifenilo H SO2CF3 CH2CH2 H
188
4-fluorofenilo H SO2CF3 CH2CH2 H
189
3,5-dibromofenilo H SO2CF3 CH2CH2 H
190
4-bromofenilo H SO2CF3 CH2CH2 H
191
3,5-dimetilfenilo H SO2CF3 CH2CH2 H
192
3-nitrofenilo H SO2CF3 CH2CH2 H
193
2,4-dibromofenilo H SO2CF3 CH2CH2 H
194
3-nitro-5-bromofenilo H SO2CF3 CH2CH2 H
195
3,5-bistrifluorometilfenilo H SO2CF3 CH2CH2 H
196
(I) H CN CH2CH2 SCSSCH2COOCH3
197
(II) Me CN CH2CH2 SCSSCH2CH2CH3
198
(I) H CN CH2CH2 SCSSCH2OMe
199
(I) H CN CH2CH2 SCSSCH2SMe
200
(I) H CN CH2CH2 SCSSCH2CO-(4-metilfenilo)
201
3-tetrahidrofuranilo H CN CH2CH2 H
202
3-tetrahidrofuranilo H CN CH2CH2 SMe
203
(I) H COPh CH2CH2 H
204
(I) H COCH2CH3 CF2 H
205
(I) H CONH2 CH2CH2 H
206
(I) H CONHMe CH2CH2 H
207
(I) H CONMe2 CH2CH2 H
208
(I) H NO2 CH2CH2 H
209
(I) H COCClF2 CH2CH2 H
210
(I) H CN fenileno H
211
(I) Me SO2CF3 CH2 H
245
(I) H COMe CH2 CN
246
(I) H COCF3 CH2 CN
(I): 6-cloro-3-piridilo (II): 5-cloro-3-tiazolilo
imagen4 imagen5 imagen6
Tabla 5
Compuesto N.º
Ar R1 B4e Y
212
(I) H CF3 H
213
(II) H CF3 H
214
(I) H OCH3 H
10
215
(I) H CF3 5-Cl
216
(I) H CF3 5-F
217
(I) H CF3 4-Cl
218
(II) H CF3 5-Cl
219
(II) H CF3 5-F
220
(II) H CF3 4-Cl
221
(I) H CF3 3-Me
222
(I) H CF3 4-Me
223
(I) H CF3 5-Ke
224
fenilo H CF3 H
225
4-clorofenilo H CF3 H
226
3-piridilo H CF3 H
227
6-cloro-5-fluoro-3-piridilo H CF3 H
228
6-trifluorometil-3-piridilo H CF3 H
229
6-fluoro-3-piridilo H CF3 H
230
5,6-dicloro-3-piridilo H CF3 H
231
6-bromo-3-piridilo H CF3 H
232
(I) H CF3 4-F
233
(I) H CF3 3-F
234
(I) H CHCl2 H
235
(I) H CCl3 H
236
(I) H CH2Cl H
237
(I) Me CF3 H
238
(I) H CHF2 H
239
(I) H CF2Cl H
240
(I) H CHClBr H
241
(I) H CHBr2 H
242
(I) H CF2CF3 H
243
2-cloro-5-pirimidinilo H CF3 H
244
(I) H CH2Br H
El compuesto N.º 212 de la Tabla 5, N-[1-((6-cloropiridin-3-il)metil)piridin-2(1H)-iliden]-2,2,2-trifluoroacetamida, tiene las siguientes propiedades físicas. Estas propiedades no se han mencionado en ninguno de los documentos de la técnica anterior.
5
(a)
En análisis de difracción de rayos X de polvo, el compuesto tiene picos de ángulos de difracción al menos en los siguientes ángulos de difracción (2θ): 8,6 ± 0,2°, 14,2 ± 0,2°, 17,5 ± 0,2°, 18,3 ± 0,2°, 19,7 ± 0,2°, 22,3 ± 0,2°, 30,9 ± 0,2°, 35,3 ± 0,2°.
(b)
En calorimetría diferencial de barrido (DSC), el compuesto exhibe un punto de fusión de 155 a 158 ºC.
10 A continuación se dan algunos ejemplos de los tipos de plagas sobre las que los agentes de control de plagas que contienen al menos uno de los compuestos de la invención de fórmula química (I) exhiben efectos de control.
Algunos ejemplos de plagas agrícolas/hortícolas incluyen plagas de lepidópteros (por ejemplo, gusano cortador
11
imagen7
imagen8
imagen9
imagen10
imagen11
imagen12
imagen13
imagen14
imagen15
Un compuesto de fórmula (Va) se puede obtener por reacción de un haluro, anhídrido, éster o similar de fórmula R2 (en la que R2 tiene el mismo significado que se ha definido en el compuesto químico (I) anterior) con un compuesto de fórmula (IIIb), en presencia o en ausencia de una base.
5 El haluro, anhídrido, éster o similar de fórmula R2 que se usa puede ser, por ejemplo, un haluro de ácido carboxílico, un haluro de carboalquiloxi, un haluro de sulfonilo, un haluro de O,O’-alquilfosforilo, un anhídrido carboxílico, un dicarbonato de dialquilo, un éster de ácido carboxílico, un éster de ácido carbónico o un cianohaluro.
La reacción se lleva a cabo preferentemente usando un disolvente, en cuyo caso se pueden usar disolventes tales
10 como amidas (por ejemplo, dimetilformamida, dimetilacetamida), nitrilos (por ejemplo, acetonitrilo), sulfóxidos (por ejemplo, dimetilsulfóxido), éteres (por ejemplo, dietil éter, tetrahidrofurano), ésteres (por ejemplo, acetato de etilo, acetato de butilo), hidrocarburos aromáticos (por ejemplo, benceno, xileno, tolueno), alcoholes (por ejemplo, metanol, etanol, propanol), cetonas (por ejemplo, acetona, metil etil cetona), hidrocarburos alifáticos (por ejemplo, hexano, heptano, octano), hidrocarburos halogenados (por ejemplo, diclorometano, cloroformo, clorobenceno,
15 diclorobenceno), o agua, individualmente o en forma de combinaciones de dos o más de los mismos. El uso de un éter tal como dietil éter o tetrahidrofurano es preferente.
Cuando la reacción se lleva a cabo en presencia de una base, la base puede ser, por ejemplo, un hidruro de metal alcalino tal como hidruro sódico, un carbonato tal como carbonato potásico o carbonato sódico, un hidróxido de
20 metal alcalino tal como hidróxido potásico o hidróxido sódico, una amina terciaria tal como trietilamina, o un compuesto de piridina sustituida o sin sustituir tal como piridina o 4-dimetilaminopiridina.
Un compuesto de fórmula (Va) se puede obtener por reacción de un compuesto de fórmula R2-NH2 (en la que R2 tiene el mismo significado que se ha definido en el compuesto químico (I) anterior) con un compuesto de fórmula
25 (IIIa), en presencia o en ausencia de una base.
El uso de un disolvente en la reacción es preferente, en cuyo caso se pueden usar disolventes tales como amidas (por ejemplo, dimetilformamida, dimetilacetamida), nitrilos (por ejemplo, acetonitrilo), sulfóxidos (por ejemplo, dimetilsulfóxido), éteres (por ejemplo, dietil éter, tetrahidrofurano), ésteres (por ejemplo, acetato de etilo, acetato de
30 butilo), hidrocarburos aromáticos (por ejemplo, benceno, xileno, tolueno), alcoholes (por ejemplo, metanol, etanol, propanol), cetonas (por ejemplo, acetona, metil etil cetona), hidrocarburos alifáticos (por ejemplo, hexano, heptano, octano), hidrocarburos halogenados (por ejemplo, diclorometano, cloroformo, clorobenceno, diclorobenceno), o agua, individualmente o en forma de combinaciones de dos o más de los mismos. El uso de acetonitrilo o similar es preferente.
35 Cuando la reacción se lleva a cabo en presencia de una base, la base puede ser, por ejemplo, un hidruro de metal alcalino tal como hidruro sódico, un carbonato tal como carbonato potásico o carbonato sódico, un hidróxido de metal alcalino tal como hidróxido potásico o hidróxido sódico, una amina terciaria tal como trietilamina, o un compuesto de piridina sustituida o sin sustituir tal como piridina o 4-dimetilaminopiridina.
40
(3) Los compuestos de fórmula (Ia) también se pueden sintetizar a partir de los compuestos de la siguiente fórmula química (Vb)
imagen16
45 (en laqueR2,R3 y R4 tienen los mismos significados que se han definido en la fórmula química (I) anterior).
Los compuestos de fórmula (Ia) se puede obtener por reacción de un compuesto de fórmula (Vb) con un compuesto de fórmula Ar-CH2-X (en la que Ar tiene el mismo significado que se ha definido en la fórmula química (I) anterior, y 50 X es un átomo de halógeno, OTs u OMs), en presencia o en ausencia de una base.
Cuando la reacción se lleva a cabo en presencia de una base, la base puede ser, por ejemplo, un hidruro de metal alcalino tal como hidruro sódico, un carbonato tal como carbonato potásico o carbonato sódico, un hidróxido de metal alcalino tal como hidróxido potásico o hidróxido sódico, una amina terciaria tal como trietilamina, o un
55 compuesto de piridina sustituida o sin sustituir tal como piridina o 4-dimetilaminopiridina. El uso de un hidruro de metal alcalino tal como hidruro sódico es preferente.
La reacción se puede llevar a cabo en ausencia de un disolvente o usando un disolvente que no afecte a la reacción. En los casos en los que se usa un disolvente, se pueden usar disolventes tales como amidas (por ejemplo,
21
imagen17
imagen18
imagen19
imagen20
imagen21
imagen22
imagen23
imagen24
imagen25
imagen26
Tabla 6
Compuesto N.º
Método de síntesis RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
1
A 2,40 (3H, s), 2,89 (2H, s), 3,35 (2H, s), 4,27 (2H, s), 7,40 (1H, d), 7,75 (1H, dd), 8,36 (1H, d) 2211 (CN)
2
A 1,32 (3H, t), 2,68 (2H, c), 2,87 (2H, t), 3,34 (2H, t), 4,27 (2H, s), 7,41 (1H, d), 7,74 (1H, dd), 8,37 (1H, d) 2211 (CN)
3
A 0,99 (3H, t), 1,69 (2H, m), 2,65 (2H, t), 2,86 (2H, t), 3,34 (2H, t), 4,27 (2H, s), 7,40 (1H, d), 7,74 (1H, dd), 8,36 (1H, d) 2211 (CN)
4
A 0,97 (3H, t), 1,69 (2H, m), 2,92 (2H, t), 4,19 (2H, s), 7,39 (1H, d), 7,71 (1H, dd), 8,33 (1H, d) 2209 (CN)
5
A 1,96 (2H, m), 2,11 (3H, s), 2,58 (2H, t), 3,11 (2H, t), 4,21 (2H, s), 7,39 (1H, d), 7,71 (1H, dd), 8,35 (1H, d) 2210 (CN)
6
E 2,76 (3H, s), 3,31 (2H, t), 3,63 (2H, t), 4,28 (2H, s), 7,38 (1H, d), 7,73 (1H, dd), 8,35 (1H, d) 2211 (CN), m/z = 318 (M+H)
7
E 1,36 (3H, t), 3,30 (2H, t), 3,36 (2H, c), 3,61 (2H, t), 4,27 (2H, s), 7,39 (1H, d), 7,73 (1H, dd), 8,36 (1H, d) m/z = 332 (M+H)
8
E 1,02 (3H, t), 1,73 (2H, m), 3,30 (2H, t), 3,34 (2H, t), 3,61 (2H, t), 4,27 (2H, s), 7,38 (1H, s), 7,73 (1H, dd), 8,36 (1H, d) m/z = 346 (M+H)
9
E 1,37 (3H, t), 2,33 (2H, t), 3,38 (2H, c), 4,42 (2H, s), 7,51 (1H, s) 2213 (CN), m/z = 338 (M+H)
10
E 1,03 (3H, t), 1,75 (2H, c), 3,32 (2H, t), 3,36 (2H, t), 3,62 (2H, t), 4,42 (2H, s), 7,51 (1H, s) 2214 (CN), m/z = 352 (M+H)
11
A 3,19 (2H, t), 3,38 (3H, s), 3,61 (2H, t), 4,30 (2H, s), 7,38 (1H, d), 7,72 (1H, dd), 8,35 (1H, d) 2212 (CN)
12
A 0,93 (3H, t), 1,39 (2H, m), 1,65 (2H, m), 2,96 (2H, t), 4,19 (2H, s), 7,38 (1H, d), 7,71 (1H, dd), 8,33 (1H, d) 2210 (CN)
13
A 2,83 (3H, s), 4,17 (2H, s), 7,41 (1H, d), 7,71 (1H, dd), 8,34 (1H, d) 2208 (CN)
14
A 1,30 (3H, t), 3,03 (2H, c), 4,20 (2H, s), 7,39 (1H, d), 7,71 (1H, dd), 8,34 (1H, d) 2210 (CN)
15
A 1,29 (6H, d), 3,15 (1H, sept), 4,20 (2H, s), 7,39 (1H, d), 7,70 (1H, dd), 8,34 (1H, d) 2210 (CN)
16
A 2,23 (6H, s), 2,54 (2H, t), 3,06 (2H, t), 4,26 (2H, s), 7,37 (1H, d), 7,73 (1H, dd), 8,34 (1H, d) 2211 (CN)
17
B 1,66 (1H, m), 1,82 (2H, m), 2,20 (1H, m), 3,03 (1H, m), 3,17 (1H, m), 4,13 (1H, t), 7,22 (1H, m), 7,68 (1H, d), 8,45 (1H, d), 8,57 (1H, s) 2207 (CN)
18
C 1,24 (3H, t), 1,65 (3H, d), 2,91 (2H, m), 4,13 (1H, c), 7,36 (1H, d), 7,72 (1H, dd), 8,30 (1H, d) 2206 (CN)
19
A 1,28 (3H, t), 3,03 (2H, c), 4,32 (2H, s), 7,47 (1H, s) 2213 (CN)
20
A 1,12, 1,17 (3H, t), 2,12, 2,17 (3H, S), 3,29, 3,41 (2H, c), 4,53, 4,55 (2H, s), 7,29, 7,35 (1H, d), 7,41, 7,63 (2H, dd), 8,27 (1H, d) 1635 (C=O)
21
A 1,13, 1,26 (3H, t), 3,36, 3,44 (2H, c), 4,60, 4,61 (2H, s), 7,31, 7,38 (1H, d), 7,54, 7,61 (1H, dd), 8,28, 8,30 (1H, d) 1691 (C=O)
22
A 1,10 (3H, m), 3,25 (2H, m), 3,74 (3H, m), 4,44 (2H, m), 7,29 (1H, m), 7,58 (1H, m), 8,28 (1H, m) 1702 (C=O)
24
A 2,12, 2,13 (3H, s), 2,14, 2,21 (3H, s), 2,62, 2,67 (2H, t), 3,46, 3,54 (2H, t), 4,60, 4,63 (2H, s), 7,30, 7,36 (1H, d), 7,51, 7,63 (1H, dd), 8,27 (1H, d) m/z = 259 (M+H)
32
25
A 2,12, 2,13 (3H, s), 2,72 (3H, t), 3,57, 3,58 (3H, t), 4,58, 4,69 (2H, s), 7,07-7,43 (6H, m), 7,68 (1H, dd), 8,37 (1H, d) m/z = 337 (M+H)
26
A 1,98 (3H, s), 2,44 (2H, t), 3,29 (2H, t), 4,37 (2H, s), 7,33 (1H, d), 7,56 (2H, dd), 7,63 (1H, td), 7,74 (1H, dd), 7,84 (2H, dd), 8,23 (1H, d) m/z = 357 (M+H)
27
A 2,10 (3H, s), 2,63 (2H, m), 3,43 (2H, m), 3,76 (3H, m), 4,52 (2H, s), 7,30 (1H, m), 7,60 (1H, m), 8,30 (1H, m) m/z = 275 (M+H)
28
A 2,07 (3H, s), 2,58 (2H, t), 3,01 (3H, s), 3,38 (2H, t), 4,42 (2H, s), 7,36 (1H, d), 7,80 (1H, dd), 8,34 (1H, d) m/z = 295 (M+H)
29
A 2,09, 2,10 (3H, s), 2,57, 2,61 (2H, t), 3,37, 3,42 (2H, t), 4,52, 4,55 (2H, s), 7,32, 7,37 (1H, d), 7,56, 7,64 (1H, dd), 8,31, 8,32 (1H, d) m/z = 245 (M+H)
30
A 1,80 (3H, m), 2,60 (2H, m), 3,50 (2H, m), 4,74 (2H, m), 7,32 (1H, d), 7,42 (5H, m), 7,53, 7,68 (1H, dd), 8,16 (1H, d) m/z = 321 (M+H)
31
A 2,11, 2,13 (3H, s), 2,67 (2H, t), 3,50, 3,58 (2H, t), 4,67, 4,74 (2H, s), 7,34, 7,38 (1H, d), 7,55, 7,62 (1H, dd), 8,30, 8,32 (1H, d) m/z =313 (M+H)
33
A 1,33 (6H, t), 2,06 (3H, s), 2,56 (2H, t), 3,09 (2H, m), 4,08 (4H, m), 4,26 (2H, m), 7,32 (1H, d), 7,72 (1H, dd), 8,33 (1H, d) m/z = 353 (M+H)
34
A 2,13 (3H, s), 2,90 (2H, t), 3,14 (2H, t), 4,19 (2H, e), 7,44 (1H, d), 8,17 (1H, dd), 8,47 (1H, d) m/z = 361 (M+H)
35
A 1,26 (3H, t), 2,98 (2H, c), 4,19 (2H, s), 7,35 (5H, m) m/z =161 (M+H)
36
A 1,29 (3H, t), 3,02 (2H, c), 4,22 (2H, s), 7,36 (1H, dd), 7,73 (1H, dd), 8,56 (1H, d), 8,62 (1H, dd) m/z =162 (M+H)
37
A 1,27 (3H, t), 3,00 (2H, c), 4,16 (2H, s), 7,27 (2H, d), 7,35 (2H, d) m/z = 195 (M+H)
39
A 1,12 (3H, tx2), 2,11, 2,18 (3H, s), 3,28, 3,43 (2H, t), 4,51, 4,59 (2H, s), 7,29 (5H, m)
40
A 1,07 (3H, m), 3,25 (2H, m), 3,74 (3H, s), 4,47 (2H, s) , 7,28 (5H, m)
41
A 1,25 (3H, t), 2,99 (2H, c), 4,20 (2H, s), 7,11 (1H, m), 7,25 (1H, m), 7,36 (1H, m) m/z = 167 (M+H)
42
A 2,54 (1H, t), 3,81 (2H, d), 4,30 (2H, s), 7,40 (1H, d), 7,73 (1H, dd), 8,39 (1H, d) m/z = 206 (M+H)
43
A 3,62 (2H, dd), 4,19 (2H, s), 5,37 (2H, ddx2), 5,85 (1H, tdd), 7,39 (1H, d), 7,71 (1H, dd), 8,33 (1H, d) m/z = 208 (M+H)
44
A 4,10 (2H, s), 4,17 (2H, a), 7,33 (6H, m), 7,65 (1H, dd), 8,23 (1H, d) m/z = 258 (M+H)
45
A 1,32 (3H, t), 3,03 (2H, c), 4,23 (2H, s), 7,53 (1H, m), 7,64 (3H, m) m/z = 186 (M+H)
46
A 1,32 (3H, t), 3,06 (2H, g), 4,31 (2H, s), 7,75 (1H, d), 7,93 (1H, dd), 8,68 (1H, d) m/z = 230 (M+H)
47
A 2,14 (3H, s), 2,78 (2H, t), 3,25 (2H, t), 4,38 (2H, s), 7,76 (1H, d), 7,97 (1H, dd), 8,72 (1H, d) m/z = 276 (M+H)
Tabla 7
Compuesto N.º
Método de síntesis RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
48
A 1,26 (3H, t), 2,56 (2H, m), 2,81 (2H, c), 3,24 (2H, t), 4,38 (2H, s), 7,75 (1H, d), 7,96 (1H, d), 8,71 (1H, s) m/z = 290 (M+H)
49
A 2,75 (2H, t), 3,05 (2H, t), 3,73 (2H, s), 4,20 (2H, s), 6,18 (1H, d), 6,31 (1H, dd), 7,35 (1H, d), 7,38 (1H, d), 7,71 (1H, dd), 8,31 (1H, d) m/z = 308 (M+H)
33
50
A 2,65 (2H, t), 2,99 (2H, t), 3,72 (2H, s), 4,11 (2H, s), 7,30 (6H, a), 7,64 (1H, dd), 8,26 (1H, d) m/z = 318 (M+H)
51
A 3,44 (2H, m), 3,48 (2H, m), 4,23 (2H, s), 7,37 (1H, d), 7,61 (2H, m), 7,70 (2H, m), 7,91 (2H, m), 8,33 (1H, d) m/z = 336 (M+H)
52
A 3,12 (2H, td), 3,17 (2H, td), 4,18 (2H, s), 7,31 (6H, m), 7,68 (1H, dd), 8,25 (1H, m) m/z = 304 (M+H)
53
A 3,43 (2H, t), 4,19 (2H, t), 4,35 (2H, s), 6,88 (2H, d), 7,02 (1H, m), 7,31 (3H, m), 7,72 (1H, dd), 8,36 (1H, d) m/z - 288 (M+H)
54
A 2,01 (3H, s), 3,17 (2H, t), 3,50 (2H, c), 4,24 (2H, s), 5,92 (1H, s a), 7,39 (1H, d), 7,69 (1H, dd), 8,36 (1H, d) m/z = 253 (M+H)
55
B 4,08 (4H, s), 7,23 (4H, d), 7,36 (4H, d) m/z = 291 (M+H)
57
E 2,96 (2H, t), 3,20 (2H, t), 4,07 (2H, s), 7,17 (2H, m), 7,29 (4H, m), 7,48 (1H, dd), 8,18 (1H, d) m/z = 272 (M+H)
58
E 3,43 (2H, t), 4,98 (2H, s), 4,53 (2H, t), 7,33 (1H, d), 7,47 (1H, a), 7,60 (1H, m), 7,71 (1H, dd), 8,03 (2H, m), 8,35 (1H, d) m/z = 316 (M+H)
59
E 3,98 (2H, s), 4,36 (2H, s), 7,45 (1H, d), 7,74 (1H, dd), 8,42 (1H, d) m/z = 207 (M+H)
61
E 2,11 (3H, s), 3,28 (2H, t), 4,27 (4H, m), 7,40 (1H, d), 7,71 (1H, dd), 8,36 (1H, d) m/z = 254 (M+H)
62
E 2,25 (3H, )), 4,17 (2H, 6), 4,33 (2H, m), 7,39 (1H, d), 7,72 (1H, dd), 8,37 (1H, d) m/z = 228 (M+H)
68
E 2,21 (1H, dd), 2,58 (1H, dd), 3,08 (2H, m), 3,32 (1H, dd), 4,31 (2H, dd), 7,39 (1H, d), 7,72 (1H, dd), 8,36 (1H, d)
69
E 2,60 (1H, dd), 2,88 (2H, m), 3,21 (1H, m), 3,49 (1H, dd), 4,31 (2H, s), 7,38 (1H, d), 7,74 (1H, dd), 8,39 (1H, d)
70
E 2,70 (2H, t), 3,30 (2H, t), 3,73 (3H, s), 4,25 (2H, s), 7,38 (1H, d), 7,72 (1H, dd), 8,35 (1H, d)
71
E 0,27 (2H, m), 0,66 (2H, m), 1,06 (1H, m), 2,88 (2H, d), 4,26 (2H, s), 7,40 (1H, d), 7,75 (1H, dd), 8,34 (1H, d) m/z = 222 (M+H)
72
A 2,14 (3H, s), 2,77 (2H, t), 3,23 (2H, t), 4,28 (2H, S), 7,87 (1H, d), 8,28 (1H, d) m/z = 276 (M+H)
73
C 1,69 (3H, d), 2,90 (3H, s), 2,77 (2H, m), 3,08 (2H, m), 4,23 (1H, c), 7,38 (1H, d), 7,76 (1H, dd), 8,33 (1H, d) m/z = 256 (M+H)
74
A 2,15 (3H, s), 2,75 (2H, t), 3,23 (2H, t), 4,24 (2H, s), 7,51 (1H, s) m/z = 248 (M+H)
75
A 1,27 (3H, t), 2,58 (2H, c), 2,78 (2H, t), 3,21 (2H, t), 4,42 (2H, a), 7,51 (1H, a) m/z = 262 (M+H)
76
A 2,22 (2H, m), 2,92 (4H, m), 3,63 (1H, m), 4,26 (2H, s), 7,39 (1H, d), 7,73 (1H, dd), 8,36 (1H, d), m/z = 254 (M+H)
77
A 1,36 (3H, d), 2,11 (3H, d), 2,62 (1H, dd), 2,79 (1H, dd), 3,15 (1H, a), 4,29 (1H, d), 4,32 (1H, d), 7,38 (1H, d), 7,76 (1H, dd), 8,37 (1H, d) m/z = 256 (M+H)
78
A 2,11 (3H, S), 2,75 (2H, t), 3,21 (2H, t), 4,27 (2H, s), 7,00 (1H, dd), 7,89 (1H, td), 8,19 (1H, d) m/z = 226 (M+H)
79
A 2,14 (3H, s), 2,78 (2H, t), 3,23 (2H, t), 4,30 (2H, s), 7,59 (1H, dd), 8,21 (1H, s) m/z = 260 (M+H)
80
A 1,30 (3H, t), 3,01 (2H, c), 4,21 (2H, s), 7,54 (1H, d), 8,19 (1H, s) m/z = 214 (M+H)
34
81
A 3,60, 3,68, 3,70 (2H, dtx2), 4,60, 4,69 (2H, tx2), 4,77, 4,78 (2H, sx2), 7,33, 7,39 (1H, dx2), 7,55, 7,63 (1H, ddx2), 8,30, 8,33 (1H, dx2) m/z = 285 (M+H)
82
A 3,30 (2H, dt), 4,31 (2H, s), 4,31-4,73 (2H, m), 7,39 (1H, d), 7,73 (1H, dd), 8,36 (1H, d) m/z = 214 (M+H)
83
E 4,18 (2H, s), 4,32 (2H, s), 7,40 (1H, d), 7,48 (1H, s) 7,69 (1H, dd), 8,33 (1H, d) m/z = 299 (M+H)
84
E 2,47 (3H, s), 3,31 (2H, t), 4,21 (2H, t), 4,23 (2H, s), 7,37 (3H, m), 7,68 (1H, dd), 7,79 (2H, d), 8,30 (1H, d) m/z = 366 (M+H)
85
F 1,22 (3H, tx2), 3,36 (2H, tx2), 3,60 (2H, tx2), 3,71 (2H, c), 4,02 (2H, c), 4,28, 4,32 (2H, sx2), 4,94, 5,31 (2H, sx2), 7,32 (6H, m), 7,74 (1H, m), 8,38 (1H, m) m/z = 405 (M+H)
86
F 1,42 (3H, t), 3,31 (2H, t), 3,38 (2H, t), 4,28 (2H, s), 4,63 (2H, c), 7,38 (1H, d), 7,72 (1H, dd), 8,37 (1H, d) m/z = 316 (M+H)
88
F 3,25, 3,47 (3H, sx2), 3,36 (2H, tx2), 3,60 (2H, tx2), 4,29, 4,32 (2H, sx2), 4,98, 5,33 (2H, sx2), 7,18-7,37 (6H, m), 7,73 (2H, m), 8,41 (1H, m) m/z = 391 (M+H)
89
C 1,74 (3H, m), 3,19 (1H, a), 3,37-3,82 (1H, m), 4,31-4,66 (2H, m), 5,33 (1H, m), 7,37 (1H, dx2), 7,57, 7,70 (1H, ddx2), 8,35, 8,38 (1H, dx2) m/z = 299 (M+H)
90
F 1,39 (6H, d), 3,30-3,40 (4H, m), 5,73 (1H, m), 7,38 (1H, d), 7,73 (1H, dd), 8,37 (1H, d) m/z = 330 (M+H)
91
F 0,92 (3H, t), 1,37 (4H, m), 1,79 (2H, m), 3,31 (2H, t), 3,38 (2H, t), 4,29 (2H, s), 4,57 (2H, t), 7,38 (1H, d), 7,73 (1H, dd), 8,37 (1H, d) m/z = 358 (M+H)
92
C 1,70 (3H, d), 3,22 (2H, m), 4,29 (1H, c), 4,64 (2H, m), 7,39 (1H, d), 7,74 (1H, dd), 8,33 (1H, d) m/z = 228 (M+H)
93
F 1,00 (3H, t), 1,38 (2H, m), 3,31 (2H, t), 3,38 (2H, t), 4,29 (2H, s), 4,53 (2H, t), 7,38 (1H, d), 7,73 (1H, dd), 8,37 (1H, d) m/z = 330 (M+H)
94
F 0,96 (3H, t), 1,41 (2H, m), 1,80 (2H, m), 3,31 (2H, t), 3,38 (2H, t), 4,28 (2H, a), 4,58 (2H, t), 7,38 (1H, d), 7,73 (1H, dd), 8,36 (1H, d) m/z = 344 (M+H)
95
A 3,68, 3,76 (2H, tdx2), 4,78, 4,88 (2H, sx2), 5,85-6,15 (1H, m), 7,52, 7,56 (1H, sx2) m/z = 309 (M+H)
96
C 1,73 (3H, d), 3,16, 3,49 (2H, mx2), 5,27, 5,37 (1H, cx2), 7,33, 7,40 (1H, dx2), 7,56, 7,70 (1H, dx2), 8,36 (1H, d) m/z = 317 (M+H)
97
A 3,60, 3,71 (2H, tdx2), 4,79 (2H, s), 5,85-6,18 (1H, m), 7,36, 7,40 (1H, dx2), 7,53, 7,60 (1H, ddx2), 8,30, 8,36 (1H, dx2) m/z = 303 (M+H)
Tabla 8
Compuesto N.º
Método de síntesis RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
98
F 3,59, 3,87 (2H, tdx2), 4,76, 4,85 (2H, Sx2), 5,86-6,17 (1H, m), 7-37, 7,41 (1H, dx2), 7,55, 7,62 (1H, dx2), 8,31, 8,32 (1H, sx2) m/z = 319 (M+H)
99
A 3,59 (2H, m), 5,11 (2H, m), 6,10 (1H, m), 7,37 (1H, d), 7,60 (1H, d), 8,32 (1H, s) m/z = 351 (M+H)
100
F 2,03 (2H, m), 2,47 (3H, s), 3,09 (2H, t), 4,12 (2H, t), 4,18 (2H, m), 7,38 (3H, m), 7,70 (1H, dd), 7,78 (1H, d), 8,33 (1H, d) m/z = 380 (M+H)
101
F 1,43 (3H, t), 2,10 (2H, m), 3,10 (2H, t), 3,20 (2H, t), 4,21 (2H, s), 4,66 (2H, c), 7,39 (1H, d), 7,71 (1H, dd), 8,34 (1H, d) m/z = 330 (M+H)
102
F 1,00 (2H, t), 1,83 (2H, c), 2,11 (2H, c), 3,09 (2H, t), 3,19 (2H, t), 4,21 (2H, s), 4,55 (2H, t), 7,38 (1H, d), 7,71 (1H, dd), 8,34 (1H, d) m/z = 344 (M+H)
103
F 1,25 (3H, m), 2,12 (2H, m), 3,06, 3,12 (2H, tx2), 3,36, 3,40 (2H, tx2), 3,71, 4,05 (2H, cx2), 4,19, 4,23 (2H, sx2), 4,94, 5,33 (2H, sx2), 7,33 (7H, m), 7,72 (1H, m), 8,33 (1H, m) m/z = 419 (M+H)
35
104
A 3,58 (2H, m), 4,67 (2H, m), 5,77-6,07 (1H, m), 7,41 (1H, d), 7,72 (1H, dd), 8,37 (1H, d)
105
C 1,01, 1,17 (3H, tx2), 1,72 (3H, dx2), 3,02-3,54 (2H, m), 5,28, 5,38 (1H, cx2), 7,34, 7,38 (1H, dx2), 7,57, 7,66 (1H, ddx2), 8,37 (1H, m) m/z = 281 (M+H)
107
C 1,02 (3H, t), 1,72 (3H, d), 3,28 (2H, m), 5,26 (1H, c), 7,37 (1H, d), 7,77 (1H, d), 8,44 (1H, d) m/z = 317 (M+H)
108
C 1,70, 1,75 (3H, dx2), 3,16-3,58 (2H, m), 5,30 (1H, c), 5,61-5,96 (1H, m), 7,38, 7,41 (1H, dx2), 7,73 (1H, dd), 8,41, 8,44 (1H, dx2) m/z = 353 (M+H)
109
C 1,01 (3H, m), 2,03, 2,24 (2H, mx2), 3,32, 3,72 (2H, mx2), 5,03 (1H, c), 5,60-6,20 (1H, m), 7,37, 7,41 (1H, dx2), 7,60, 7,76 (1H, ddx2), 8,39 (1H, d) m/z = 331 (M+H)
110
C 0,97 (3H, t), 2,04-2,32 (2H: m), 3,30-3,60 (2H, m), 5,72-6,00 (1H, m), 7,41 (1H, d), 7,72 (1H, m), 8,44 (1H, s) m/z = 367 (M+H)
111
C 1,02 (3H, m), 2,00-2,30 (2H, m), 3,14-3,38 (2H, m), 4,94-5,12 (1H, m), 7,26-7,34 (1H, m), 7,60-7,76 (1H, m), 8,38 (1H, m) m/z = 295 (M+H)
112
C 0,98, 1,05 (3H, t), 2,06, 2,24 (2H, mx2), 3,32 (2H, m), 4,90 (1H, c), 7,38 (1H, d), 7,75 (1H, m), 8,45 (1H, s) m/z = 331 (M+H)
114
C 1,03 (3H, t), 1,78 (3H, d), 3,20-3,45 (2H, m), 5,32 (1H, c), 7,73 (1H, d), 7,98 (1H, d), 8,82 (1H, s) m/z = 351 (M+H)
115
C 1,03, 1,23 (3H, tx2), 1,78 (3H, dx2), 3,00-3,60 (2H, m), 5,34 (1H, c), 7,69, 7,73 (1H, dx2), 7,80, 7,88 (1H, dx2), 8,70, 8,71 (1H, dx2) m/z = 315 (M+H)
119
E 3,63 (2H, d), 4,33 (2H, s), 5,38 (2H, m), 5,83 (1H, m), 7,47 (1H, s) m/z = 214 (M+H)
120
E 2,55 (1H, t), 3,83 (2H, d), 4,46 (2H, s), 7,55 (1H, s) m/z = 212 (M+H)
121
E 2,86 (3H, s), 4,31 (2H, s), 7,50 (1H, s) m/z = 188 (M+H)
122
E 0,98 (3H, t), 1,69 (2H, m), 2,95 (2H, t), 4,33 (2H, s), 7,49 (1H, s) m/z = 216 (M+H)
124
C 0,95 (3H, m), 1,73 (3H, d), 3,47 (2H, m), 5,22 (1H, m), 7,25 (2H, m), 7,71 (1H, td), 8,58 (1H, d) m/z = 283 (M+H)
128
A 2,50 (1H, t), 4,23 (2H, m), 4,71 (2H, m), 7,41 (1H, d), 7,75 (1H, dd), 8,41 (1H, d) m/z = 313 (M+H)
129
A 3,96 (2H, m), 4,55 (2H, m), 7,44 (1H, d), 7,74 (1H, dd), 8,44 (1H, d) m/z = 314 (M+H)
130
A 1,23 (3H, tx2), 3,49 (2H, cx2), 4,86 (2H, sx2), 7,56 (1H, dx2), 8,58 (1H, sx2), 8,74 (1H, dx2) m/z = 301 (M+H)
131
A 1,20 (3H, t), 3,42 (2H, m), 4,64 (2H, m), 7,74 (1H, d), 7,96 (1H, dd), 8,70 (1H, d) m/z = 337 (M+H)
132
C 1,04, 1,16, 1,31 (3H, tx3), 1,70 (3H, dx2), 2,90-3,58 (2H, m), 5,25, 5,40 (1H, cx2), 7,22, 7,34 (2H, dx2), 8,60, 8,65 (2H, dx2) m/z = 247 (M+H)
133
C 0,97, 1,10 (3H, tx2), 1,73 (3H, d), 3,07-3,52 (2H, m), 5,32, 5,52 (1H, cx2), 7,34 (1H, m), 7,62, 7,70 (1H, dx2), 8,56, 8,60 (1H, dx2) m/z = 247 (M+H)
134
C 0,92, 1,08 (3H, tx2), 1,71 (3H, d), 3,18-3,58 (2H, m), 5,28, 5,53 (1H, cx2), 7,20-7,36 (2H, m), 7,69 (1H, m), 8,57, 8,62 (1H, dx2) m/z = 247 (M+H)
135
A 2,94 (3H, s), 4,52 (2H, m), 7,39 (1H, d), 7,71 (1H, dd), 8,34 (1H, d) m/z = 289 (M+H)
136
E 2,47 (3H, s), 3,33 (2H, t), 4,22 (2H, t), 4,39 (2H, s), 7,38 (2H, d), 7,48 (1H, s), 7,81 (2H, d) m/z = 372 (M+H)
36
137
F 1,43 (3H, t), 3,37 (4H, m), 4,43 (2H, s), 4,67 (2H, c), 7,51 (1H, s) m/z = 322 (M+H)
138
F 1,26 (3H, t), 3,40 (2H, tx2), 3,60 (2H, tx2), 3,74, 4,06 (2H, cx2), 4,43, 4,48 (2H, sx2), 4,95, 5,30 (2H, sx2), 7,20-7,40 (5H, m), 7,53, 7,56 (1H, sx2) m/z = 411,0286 (M+H)
139
A 2,70 (3H, a), 2,97 (1H, m), 3,10 (1H, m), 3,51 (2H, m), 4,31 (2H, dd), 7,40 (1H, d), 7,76 (1H, dd), 8,40 (1H, d) m/z = 258 (M+H)
140
A 1,53 (6H, d), 4,24 (1H, m), 4,54 (2H, m), 7,35 (1H, d), 7,81 (1H, dd), 8,37 (1H, d) m/z = 317 (M+H)
141
A 0,83 (3H, t), 1,22 (2H, m), 1,55 (2H, m), 3,28 (2H, m), 4,61 (2H, m), 7,40 (1H, d), 7,74 (1H, dd), 8,34 (1H, d) m/z = 331 (M+H)
142
A 3,23 (2H, m), 3,70 (2H, m), 4,60 (2H, m), 7,24 (2H, m), 7,24-7,83 (7H, m), 8,32 (1H, d) m/z = 443 (M+H)
143
A 3,70 (2H, m), 4,11 (2H, m), 4,74 (2H, m), 6,81 (2H, m), 7,26 (1H, d), 7,34 (3H, m), 7,75 (1H, d), 8,41 (1H, s) m/z = 395 (M+H)
144
A 1,16 (3H, t), 3,39 (2H, m), 4,74 (2H, m), 7,39 (1H, d), 7,75 (1H, dd), 8,35 (1H, d) m/z = 303 (M+H)
145
A 0,84 (3H, t), 1,53 (2H, m), 3,25 (2H, t), 4,55 (2H, m), 7,37 (1H, d), 7,76 (1H, dd), 8,32 (1H, d) m/z = 317 (M+H)
146
A 3,99 (2H, a), 4,72 (2H, m), 5,22 (1H, dd), 5,36 (1H, dd), 5,71 (1H, m), 7,39 (1H, d), 7,72 (1H, dd), 8,29 (1H, d) m/z = 315 (M+H)
147
A 4,44 (4H, m), 7,18 (2H, m), 7,25 (1H, d), 7,33 (2H, m), 7,53 (1H, dd), 8,03 (1H, d) m/z = 365 (M+H)
148
A 1,30 (3H, t), 3,05 (2H, c), 4,21 (2H, s), 7,00 (1H, dd), 7,86 (1H, td), 8,18 (1H, d) m/z = 180 (M+H)
149
A 1,29 (3H, t), 3,02 (2H, c), 4,18 (2H, s), 7,53 (1H, d), 7,61 (1H, dd), 8,32 (1H, d) m/z = 240 (M+H)
Tabla 9
Compuesto N.º
Método de síntesis RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
150
A 2,15 (6H, s), 3,36 (2H, t), 4,60 (4H, m), 7,38 (1H, d), 7,76 (1H, dd), 8,36 (1H, d) m/z = 346 (M+H)
151
A 1,04 (3H, t), 3,37 (2H, c), 4,52 (2H, s), 7,37 (1H, d), 7,80 (1H, dd), 8,32 (1H, d) m/z = 401 (M+H)
152
A 2,07 (1H, t), 2,43 (2H, m), 3,48 (2H, t), 4,69 (2H, m), 7,40 (1H, d), 7,76 (1H, dd), 8,36 (1H, d) m/z = 327 (M+H)
153
A 1,32 (3H, t), 3,06 (2H, c), 4,21 (2H, s), 7,23 (1H, dd), 7,31 (1H, d), 8,42 (1H, d) m/z = 196 (M+H)
154
A 1,30 (3H, t), 3,14 (2H, c), 4,31 (2H, s), 7,30 (1H, d), 7,38 (1H, d), 7,72 (1H, dd) m/z = 196 (M+H)
155
A 3,29 (3H, s), 3,45 (4H, m), 4,68 (2H, m), 7,36 (1H, d), 7,74 (1H, dd), 8,37 (1H, d) m/z = 333 (M+H)
157
A 1,17, 1,31 (3H, tx2), 3,48, 3,63 (2H, cx2), 7,52 (1H, d), 7,60 (1H, d) m/z = 268 (M+H)
158
A 1,30 (3H, t), 3,01 (2H, c), 4,13 (2H, s), 7,23 (2H, s), 7,35 (1H, e) m/z = 229 (M+H)
159
A 2,58 (2H, m), 3,61 (2H, t), 4,52 (2H, m), 7,43 (1H, d), 7,78 (1H, dd), 8,41 (1H, d) m/z = 328 (M+H)
37
160
A 3,75 (3H, s), 3,94 (2H, m), 4,71 (2H, m), 7,39 (1H, d), 7,72 (1H, dd) , 8,29 (1H, d) m/z = 347 (M+H)
161
A 4,03 (2H, m), 4,74 (2H, m), 7,40 (1H, d), 7,73 (1H, dd), 8,31 (1H, d) m/z = 333 (M+H)
163
A 4,26 (2H, m), 4,82 (2H, m), 7,63 (1H, a) m/z = 320 (M+H)
165
A 4,02 (2H, a), 4,84 (2H, m), 7,79 (1H, d), 8,00 (1H, dd), 8,78 (1H, d) m/z = 348 (M+H)
167
A 4,20 (2H, m), 4,64 (2H, m), 7,58 (1H, dd), 8,27 (1H, d) m/z = 332 (M+H)
170
C 1,90 (3H, d), 3,83 (1H, d), 4,27 (1H, d), 5,42 (1H, c), 7,43 (1H, d), 7,76 (1H, dd), 8,47 (1H, d) m/z = 328 (M+H)
171
C 1,86 (3H, d), 2,28 (1H, t), 3,78 (1H, d), 4,17 (1H, d), 5,34 (1H, c), 7,37 (1H, d), 7,78 (1H, d), 8,47 (1H, d) m/z = 327 (M+H)
172
A 2,51 (1H, t), 4,25 (2H, m), 4,81 (2H, m), 7,56 (1H, s) m/z = 319 (M+H)
176
A 1,62 (3H, t), 3,40 (2H, m), 4,03 (2H, m), 7,24 (2H, d), 7,36 (1H, d) m/z = 335 (M)
177
A 1,12 (3H, t), 3,36 (2H, m), 4,57 (2H, m), 7,38 (5H, m)
178
A 1,10 (3H, m), 3,31 (2H, a), 3,81 (2H, m), 4,43 (2H, a), 7,38 (1H, d), 7,78 (1H, dd), 8,33 (1H, d) m/z = 317 (M+H)
179
A 2,51 (1H, t), 3,97 (4H, m), 4,52 (2H, s), 7,37 (1H, d), 7,75 (1H, dd), 8,37 (1H, d) m/z = 327 (M+H)
180
A 1,14 (3H, t), 3,39 (2H, m), 4,50 (2H, m), 7,26 (2H, m), 7,34 (3H, m) m/z = 301 (M)
181
A 1,12 (3H, t), 3,36 (2H, m), 4,60 (2H, m), 7,30 (2H, d), 7,36 (2H, d) m/z = 301 (M)
182
A 1,15 (3H, m), 3,39 (2H, m), 4,50 (2H, m), 7,54 (1H, m), 7,67 (3H, m) m/z = 292 M)
183
A 1,16 (2H, t), 3,42 (2H, m), 4,50 (2H, m), 7,54 (2H, d), 8,27 (2H, d) m/z = 312 (M)
184
A 2,50 (1H, t), 4,00 (2H, m), 4,65 (2H, m), 7,27 (2H, m), 7,38 (1H, m) m/z = 345 (M)
185
A 1,11 (3H, t), 2,36 (3H, t), 3,34 (2H, m), 4,49 (2H, m), 7,20 (2H, d), 7,24 (2H, d) m/z = 281 (M)
186
A 1,14 (3H, t), 3,39 (2H, m), 4,62 (2H, m), 7,48 (2H, d), 7,69 (2H, d) m/z = 292 (M)
187
A 1,11 (3H, t), 3,34 (2H, m), 3,82 (3H, s), 4,40 (2H, m), 6,88 (2H, d), 7,26 (2H, d) m/z = 297 (M)
188
A 1,12 (3H, t), 3,36 (2H, m), 4,51 (2H, m), 7,07 (2H, m), 7,33 (2H, m) m/z = 285 (M)
189
A 1,16 (3H, t), 3,40 (2H, m), 4,50 (2H, m), 7,43 (2H, d), 7,66 (1H, d)
190
A 1,12 (3H, t), 3,36 (2H, m), 4,56 (2H, m), 7,24 (2H, d), 7,52 (2H, d) m/z = 345 (M)
191
A 1,12 (3H, t), 2,32 (6H, s), 3,36 (2H, m), 4,51 (2H, m), 6,94 (2H, s), 6,97 (1H, s) m/z = 295 (M)
192
A 1,17 (3H, t), 3,42 (2H, m), 4,63 (2H, m), 7,62 (1H, m), 7,75 (1H, d), 8,20 (1H, s), 8,22 (1H, d) m/z = 312 (M)
193
A 1,17 (3H, t), 3,43 (2H, m), 4,62 (2H, m), 7,37 (1H, d), 7,52 (1H, dd), 7,74 (1H, d) m/z = 423 (M)
38
194
A 1,92 (3H, t), 3,45 (2H, m), 4,60 (2H, m), 7,87 (1H, s), 8,14 (1H, s), 8,38 (1H, s) m/z = 390 (M)
195
A 1,19 (3H, t), 3,43 (2H, m), 4,68 (2H, m), 7,81 (2H, s), 7,89 (1H, s) m/z = 403 (M)
196
E 3,32 (2H, t), 3,63 (2H, t), 3,76 (3H, s), 4,19 (2H, a), 4,27 (2H, s), 7,39 (1H, d), 7,73 (1H, dd), 8,35 (1H, d) 1740 (C=O), 2212 (CN)
198
E 3,32 (2H, t), 3,40 (3H, s), 3,63 (2H, t), 4,28 (2H, s) 5,46 (2H, s), 7,39 (1H, d), 7,73 (1H, dd), 8,36 (1H, d) 2212 (CN)
199
E 2,22 (3H, s), 3,31 (2H, t), 3,63 (2H, t), 4,27 (2H, s), 4,46 (2H, s), 7,39 (1H, d), 7,73 (1H, dd), 8,36 (1H, d) 2212 (CN)
200
E 2,44 (3H, s), 3,31 (2H, t), 3,62 (2H, t), 4,26 (2H, s), 4,89 (2H, s), 7,30 (2H, d), 7,39 (1H, d), 7,72 (1H, dd), 7,90 (2H, d), 8,34 (1H, d) 1684 (C=O), 2211 (CN)
201
A 1,29 (3H, t), 1,63 (1H, m), 2,13 (1H, m), 2,63 (1H, m), 2,99 (2H, m), 3,08 (2H, m), 3,57 (1H, m), 3,76 (1H, c), 3,87 (2H, m) 2209 (CN)
202
A 1,64 (1H, m), 2,15 (4H, m), 2,75 (2H, t), 3,04 (2H, m), 3,24 (2H, t), 3,69 (1H, dd), 3,76 (1H, c), 3,86 (2H, m) 2207 (CN)
203
A 1,12 (3H, m), 3,25 (2H, m), 4,56 (2H, m), 7,32 (1H, d), 7,75 (1H, m), 8,37 (1H, m) 1632, 1456, 1388
204
A 1,16, 1,24 (3H, tx2), 3,31, 3,45 (2H, cx2), 4,58, 4,66 (2H, sx2), 6,16 (2H, td), 7,31, 7,36 (1H, dx2), 7,56, 7,61 (1H, ddx2), 8,30 (1H, d)
205
A 1,14 (3H, t), 3,23 (2H, c), 4,48 (2H, s), 5,08 (2H, s a), 7,29 (1H, d), 7,62 (1H, dd), 8,27 (1H, s)
206
A 1,13 (3H, t), 2,83 (3H, a), 3,20 (2H, c), 4,44 (1H, s a), 4,49 (2H, s), 7,27 (1H, d), 7,64 (1H, dd), 8,27 (1H, s)
207
A 1,14 (3H, t), 2,84 (6H, s), 3,14 (2H, m), 4,29 (2H, s), 7,25 (1H, d) , 7,63 (1H, d), 8,30 (1H, s)
208
A 1,19 (3H, t), 3,85 (2H, c), 5,06 (2H, a), 7,35 (1H, d), 7,73 (1H, dd), 8,27 (1H, d) m/z = 216 (M;H)
211
C 1,70 (3H, d), 2,81 (3H, s), 5,33 (1H, c), 7,38 (1H, d), 7,71 (1H, dd), 8,41 (1H, d) 1463, 1380, 1237
Ejemplo de Síntesis 14: N-[1-((6-cloropiridin-3-il)metil)piridin-2(1H)-iliden]-2,2,2-trifluoroacetamida (Compuesto 212)
(1) Se disolvió 2-aminopiridina en una cantidad de 25 g (270 mmol) en 200 ml de diclorometano anhidro, se
5 añadieron 41 ml (30 g, 300 mmol) de trietilamina, y la mezcla se enfrió a 0 ºC. A continuación, se añadieron gota a gota 38 ml (57 g, 270 mmol) de anhídrido trifluoroacético durante 15 minutos, y la mezcla se agitó a temperatura ambiente durante 2 horas. Después de que se completara la reacción, la mezcla de reacción se vertió en aproximadamente 100 ml de agua en hielo y se agitó durante 10 minutos. La mezcla se transfirió a continuación a un embudo de decantación y se llevó a cabo una extracción líquido-líquido. La fase orgánica se
10 lavó dos veces con 150 ml de agua, se lavó dos veces con 150 ml de una solución acuosa al 1 % de HCl, a continuación se secó sobre sulfato de magnesio anhidro y se concentró a presión reducida, para dar 36 g de 2,2,2-trifluoro-N-(piridin-2(1 H)-iliden)acetamida (rendimiento, 71 %). RMN 1H (CDCl3, δ, ppm): 7,20 (1H, ddd), 7,83 (1H, td), 8,20 (1H, d), 8,35 (1H, d), 10,07 (1H, s a), RMN 13C (CDCl3, δ, ppm): 115,3, 115,5 (c), 121,6, 139,1, 147,9, 149,5, 155,3 (c),
15 MS: m/z = 191 (M+H).
(2) Se disolvió 2-cloro-5-clorometilpiridina en una cantidad de 20 g (126 mmol) en 200 ml de acetonitrilo anhidro, a continuación se añadieron 24 g (126 mmol) de 2,2,2-trifluoro-N-(piridin-2(1H)-iliden)acetamida obtenida mediante el método anterior y 21 g (151 mmol) de carbonato potásico y se llevó a cabo un calentamiento reflujo durante 6 horas, seguido de 10 horas de agitación a temperatura ambiente. Después de que se completara la
20 reacción, la mezcla de reacción se filtró, y el filtrado se concentró a presión reducida. Se añadió dietil éter al concentrado para efectuar la cristalización, y los cristales resultantes se recogieron por filtración, y a continuación se lavaron exhaustivamente con dietil éter y agua. Los cristales obtenidos de ese modo se secaron a 60 ºC y presión reducida durante 1 hora, para dar 26 g del compuesto diana (rendimiento, 66 %).
39
imagen27
imagen28
imagen29
imagen30
imagen31
se secó a presión reducida, para proporcionar el compuesto diana en una cantidad de 92 mg (rendimiento, 58 %). RMN 1H (CDCl3, δ, ppm): 5,54 (2H, s), 6,98 (1H, m), 7,87 (1H, m), 8,18 (1H, m), 8,48 (1H, m), 8,83 (2H, m); RMN 13C (CDCl3, δ, ppm): 60,0, 115,6, 117,1 (c), 122,1, 127,5, 139,2, 142,9, 158,8, 160,3 (2C), 161,4, 163,8 (c); MS: m/z = 317 (M+H).
Los datos espectrales para los compuestos obtenidos mediante métodos similares a los de los Ejemplos de Síntesis 14 a 25 se muestran en las Tablas 10 y 11.
Tabla 10
N.º
RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
212
5,57 (2H, s), 6,92 (1H, td), 7,31 (1H, d), 7,80 (1H, td), 7,87 (1H, dd), 7,99 (1H, dd), 8,48 (2H, m) m/z = 316 (M+H)
213
5,61 (2H, s), 6,93 (1H, dd), 7,68 (1H, s), 7,83 (1H, td), 7,97 (1H, d), 8,53 (1H, d) m/z = 322 (M+H)
214
3,74 (3H, s), 5,40 (2H, s), 6,45 (1H, td), 7,29 (1H, d), 7,46 (2H, m), 7,73 (1H, dd), 8,12 (1H, dd), 8,40 (1H, d) m/z = 278 (M+H)
215
5,53 (2H, s), 7,34 (1H, d), 7,71 (1H, dd), 7,87 (1H, dd), 7,94 (1H, s), 8,49 (1H, d), 8,55 (1H, s) m/z = 350 (M+H)
216
5,54 (2H, s), 7,34 (1H, d), 7,70 (1H, m), 7,80 (1H, m), 7,88 (1H, dd), 8,48 (1H, d), 8,64 (1H, m) m/z = 334 (M+H)
217
5,49 (2H, s), 6,85 (1H, dd), 7,35 (1H, d), 7,76 (1H, dd), 7,85 (1H, dd), 8,44 (1H, d), 8,62 (1H, s) m/z = 350 (M+H)
218
5,56 (2H, s), 7,68 (1H, s), 7,74 (1H, dd), 7,84 (1H, d), 8,58 (1H, d) m/z = 356 (M+H)
219
5,60 (2H, s), 7,69 (1H, s), 7,72 (1H, td), 7,86 (1H, m), 8,67 (1H, m) m/z = 340 (M+H)
220
5,58 (2H, s), 6,90 (1H, d), 7,67 (1H, s), 7,90 (1H, d), 8,61 (1H, s) m/z = 356 (M+H)
221
2,31 (3H, s), 5,50 (2H, s), 6,98 (1H, m), 7,34 (1H, d), 7,73 (1H, dd), 7,77 (2H, m), 8,42 (1H, d) m/z = 330 (M+H)
222
2,40 (3H, S), 5,49 (2H, s), 6,70 (1H, dd), 7,32 (1H, d), 7,70 (1H, d), 7,86 (1H, dd), 8,37 (1H, s), 8,43 (1H, d) m/z = 330 (M+H)
223
2,29 (3H, s), 5,52 (2H, s), 7,32 (1H, d), 7,62 (1H, s), 7,65 (1H, dd), 7,88 (1H, dd), 8,46 (1H, d), 8,50 (1H, d) m/z = 330 (M+H)
224
5,58 (2H, s), 6,81 (1H, m), 7,37 (4H, m), 7,77 (2H, m), 8,50 (1H, d) m/z = 281 (M+H)
225
5,52 (2H, s), 6,85 (1H, m), 7,30 (2H, d), 7,36 (2H, d), 7,75 (1H, td), 7,84 (1H, d), 8,47 (1H, d) m/z = 315 (M+H)
226
5,57 (2H, s), 6,86 (1H, m), 7,26-7,35 (2H, m), 7,78 (1H, td), 7,86 (1H, m), 8,63 (2H, m), 8,67 (1H, d) m/z = 282 (M+H)
227
5,54 (2H, s), 6,89 (1H, td), 7,76 (1H, dd), 7,80 (1H, td), 7,85 (1H, d), 8,29 (1H, d), 8,57 (1H, d) m/z = 334 (M+H)
228
5,62 (2H, s), 6,90 (1H, t), 7,69 (1H, d), 7,81 (1H, t), 7,88 (1H, d), 8,06 (1H, d), 8,56 (1H, d), 8,78 (1H, s) m/z = 350 (M+H)
229
5,56 (2H, s), 6,89 (1H, td), 6,94 (1H, d), 7,79 (1H, td), 7,87 (1H, d), 8,03 (1H, m), 8,31 (1H, s), 8,54 (1H, d) m/z = 300 (M+H)
230
5,49 (2H, s), 6,89 (1H, t), 7,79-7,90 (2H, m), 8,04 (1H, d), 8,37 (1H, d), 8,56 (1H, m) m/z = 350 (M+H)
231
5,52 (2H, s), 6,88 (1H, t), 7,48 (1H, d), 7,78 (2H, m), 7,84 (1H, d), 8,44 (1H, d), 8,53 (1H, d) m/z = 360 (M+H)
232
5,52 (2H, s), 6,71 (1H, m), 7,35 (1H, d), 7,86 (1H, dd), 7,94 (1H, m), 8,33 (1H, dd), 8,44 (1H, d) m/z = 334 (M+H)
233
5,53 (2H, s), 6,74 (1H, m), 7,33 (1H, d), 7,87 (1H, dd), 8,07 (1H, m), 8,29 (1H, dd), 8,45 (1H, d) m/z = 334 (M+H)
45
234
5,54 (2H, s), 6,02 (1H, s), 6,77 (1H, t), 7,32 (1H, m), 7,69 (1H, m), 7,77 (1H, d), 7,89 (1H, m), 8,42 (1H, m), 8,49 (1H, s) m/z = 330 (M+H)
Tabla 11
N.º
RMN 1H (CDCl3, δ, ppm) IR (HBr, ν, cm1) o MS
235
5,59 (2H, s), 6,86 (1H, t), 7,32 (1H, d), 7,78 (1H, td), 7,91 (2H, m), 8,43 (1H, d), 8,50 (1H, d) m/z = 364 (M+H)
236
4,17 (2H, s), 5,46 (2H, s), 6,64 (1H, td), 7,31 (1H, d), 7,60 (1H, td), 7,64 (1H, dd), 7,80 (1H, dd), 8,32 (1H, d), 8,45 (1H, d) m/z = 296 (M+H)
237
1,89 (3H, d), 6,89 (1H, td), 7,08 (1H, c), 7,32 (1H, d), 7,66 (1H, dd), 7,76 (2H, m), 8,44 (1H, d), 8,50 (1H, d) m/z = 330 (M+H)
238
5,52 (2H, s), 5,90 (1H, t), 6,79 (1H, td), 7,33 (1H, d), 7,71 (1H, m), 7,77 (1H, dd), 7,85 (1H, dd), 8,45 (1H, d), 8,50 (1H, d) m/z = 298 (M+H)
239
5,56 (2H, s), 6,92 (1H, t), 7,33 (1H, d), 7,82 (1H, m), 7,91 (1H, dd), 8,02 (1H, d), 8,45 (1H, d), 8,48 (1H, d) m/z = 332 (M+H)
240
5,53 (1H, d), 5,58 (1H, d), 6,06 (1H, s), 6,76 (1H, td), 7,32 (1H, d), 7,69 (1H, m), 7,70 (1H, m), 7,90 (1H, dd), 8,40 (1H, d), 8,50 (1H, d) m/z = 374 (M+H)
241
5,56 (2H, s), 5,99 (1H, s), 6,78 (1H, td), 7,33 (1H, d), 7,69 (1H, td), 7,76 (1H, dd), 7,93 (1H, dd), 8,39 (1H, d), 8,50 (1H, d) m/z = 418 (M+H)
242
5,56 (2H, s), 6,90 (1H, td), 7,32 (1H, d), 7,79 (2H, m), 7,84 (1H, d), 8,43 (1H, d), 8,56 (1H, d) m/z = 366 (M+H)
243
5,54 (2H, s), 6,98 (1H, m), 7,87 (1H, m), 8,18 (1H, m), 8,48 (1H, m), 8,83 (2H, m) m/z = 317 (M+H)
244
4,17 (2H, s), 5,46 (2H, s), 6,63 (1H, td), 7,31 (1H, d), 7,60 (1H, td), 7,65 (1H, dd), 7,80 (1H, dd), 8,32 (1H, d), 8,47 (1H, d)
Ejemplo Comparativo 1: N-[(6-cloropiridin-3-il)metil]cianamida (documento de Patente JP 2003-26661 A, Compuesto 5 1)
Se disolvió bromuro de cianógeno (220 mg, 2,09 mmol) en 10 ml de cloroformo anhidro, y la solución se enfrió a 0 ºC. A esto se añadió gota a gota a gota una solución de 500 mg (3,49 mmol) de 2-cloro-5-aminometilpiridina disuelta en 10 ml de cloroformo anhidro, y la mezcla resultante se agitó a 0 ºC durante 1 hora. La mezcla de reacción
10 se filtró, a continuación se añadió agua y se llevó a cabo una extracción líquido-líquido, después de lo cual la fase de cloroformo se secó sobre sulfato de magnesio anhidro y se concentró a presión reducida. El concentrado se purificó por cromatografía en columna sobre gel de sílice (hexano/acetato de etilo = 1:1), para dar 122 mg (rendimiento, 35 %) del compuesto diana. RMN 1H (CDCl3, δ, ppm): 4,21 (2H, s), 5,74 (1H, s a), 7,36 (1H, d), 7,71 (1H, dd), 8,30 (1H, d);
15 RMN 13C (CDCl3, δ, ppm): 46,5, 116,1, 124,8, 131,5, 138,9, 148,9, 151,4; MS: m/z = 166 (M-H).
Ejemplo Comparativo 2: N-[1-((6-cloropiridin-3-il)metil)piridin-2(1H)-iliden]cianamida (Documento de Patente 6, Compuesto 20) 20
imagen32
Una cantidad de 128 mg (0,58 mmol) de 1-[(6-cloropiridin-3-il)metil]piridina-2(1H)-imina obtenida mediante el método alternativo que se ha descrito en el Ejemplo de Síntesis 14 se disolvió en 5 ml de dimetilformamida anhidra, se añadió NaH (en forma de una dispersión al 60 % en aceite) en una cantidad de 40 mg (peso neto, 24 mg;
46
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imagen41
imagen42
imagen43
imagen44
imagen45
imagen46
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imagen48
Además, los efectos frente a plagas que tienen una baja susceptibilidad a insecticidas de los Compuestos con números 212, 227, 229, 231, 237, 238, 239, 242 y 243, que son compuestos especialmente preferentes de acuerdo con la divulgación, se resumen en la Tabla 13.
Tabla 13
Cigarras marrón pequeña (empapado de suelo de arroz)
Cigarras marrón del arroz, baja susceptibilidad de Kumamoto (empapado de suelo de arroz)
0,05 mg/m aceta
0,01 mg/m aceta 0,005 mg/ maceta 0,002 mg/ maceta 0,05 mg/maceta 0,005 mg/maceta
212
100 100 95 85 100 90
227
90 100 75 imagen49 imagen50 imagen51
229
100 100 30 imagen52 imagen53 imagen54
231
100 100 70 imagen55 imagen56 imagen57
237
100 75 imagen58 imagen59 imagen60 imagen61
238
100 100 33 imagen62 imagen63 imagen64
239
100 80 30 imagen65 imagen66 imagen67
242
100 imagen68 imagen69 imagen70 imagen71 imagen72
243
100 imagen73 imagen74
Ejemplo Comparativo 2 (Documento de Patente 6, Compuesto 20)
20
Ejemplo Comparativo 3 (Documento de Patente 4, Compuesto 2)
10
Ejemplo Comparativo 4 (Documento de Patente 5, Ejemplo 4)
100 20 45
Ejemplo Comparativo 5 (Documento de Patente 5, Ejemplo 3)
95 15 25
Ejemplo Comparativo 6 (Documento de Patente 5, Ejemplo 5)
100 20 25
Ejemplo Comparativo 7 (Documento de Patente 5, Ejemplo 7)
63 5 20
Ejemplo Comparativo 8 (Documento de Patente 5, Ejemplo 6)
20
Aplicabilidad industrial
El derivado de amina de la presente invención tiene excelentes efectos insecticidas frente a la polilla dorso de
10 diamante, el gusano cortador común, el pulgón del algodón, la cigarra marrón pequeña, la cigarra marrón del arroz, el saltahojas verde del arroz, la garrapata de cuerpo duro Haemaphysalis longicornis, y muchas otras plagas. Además, es capaz de exhibir potentes efectos incluso frente a insectos que tienen una baja susceptibilidad a insecticidas, particularmente cigarras delfácidos. Además, también es eficaz en el tratamiento de suelos y medios de cultivo de plantas y, debido a que es capaz de mitigar los riesgos de la exposición a productos químicos del
15 trabajador, se puede usar de forma segura para controlar plagas. Por lo tanto, la presente invención puede ser altamente beneficiosa en el campo del control de plagas.
También se desvela:
63
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Families Citing this family (334)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102892290B (zh) * 2010-08-31 2016-02-03 明治制果药业株式会社 有害生物防除剂
EP2749555B1 (en) * 2011-08-26 2018-11-14 Meiji Seika Pharma Co., Ltd. Method for producing pest controlling agent
BR112014020831B8 (pt) 2012-02-29 2022-11-22 Meiji Seika Pharma Co Ltd Composição de controle de peste incluindo derivado de iminopiridina, seu uso e método para pro-teger plantas úteis de pestes
JP6236396B2 (ja) * 2012-02-29 2017-11-22 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 ２−イミノ基を有する含窒素ヘテロ環誘導体及びそれを含んでなる有害生物防除剤
JP2015512905A (ja) 2012-03-29 2015-04-30 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有害動物を駆除するためのｎ−置換複素二環式化合物および誘導体ｉｉ
EP2830421B1 (en) 2012-03-30 2017-03-01 Basf Se N-substituted pyridinylidene thiocarbonyl compounds and their use for combating animal pests
WO2013144223A1 (en) 2012-03-30 2013-10-03 Basf Se N-substituted pyrimidinylidene compounds and derivatives for combating animal pests
ES2656543T3 (es) 2012-05-24 2018-02-27 Basf Se Compuestos de N-tio-antranilamida y su uso como pesticidas
JP2015525223A (ja) 2012-06-14 2015-09-03 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 動物有害生物を駆除するための置換３−ピリジルチアゾール化合物および誘導体を使用する有害生物防除方法
WO2014005982A1 (de) 2012-07-05 2014-01-09 Bayer Cropscience Ag Insektizide und fungizide wirkstoffkombinationen
US20150237858A1 (en) 2012-10-01 2015-08-27 Basf Se Method of controlling ryanodine-modulator insecticide resistant insects
WO2014053401A2 (en) 2012-10-01 2014-04-10 Basf Se Method of improving plant health
WO2014053407A1 (en) 2012-10-01 2014-04-10 Basf Se N-thio-anthranilamide compounds and their use as pesticides
AR093771A1 (es) 2012-10-01 2015-06-24 Basf Se Metodo para controlar insectos resistentes a insecticidas
AU2013326645A1 (en) 2012-10-01 2015-04-23 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
US20150250175A1 (en) 2012-10-01 2015-09-10 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
BR112015004074A2 (pt) 2012-10-01 2017-07-04 Basf Se método para controlar pragas, uso e semente de uma planta cultivada.
WO2014079766A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
EP2922399B1 (en) 2012-11-22 2020-02-26 Basf Corporation Pesticidal mixtures
WO2014079772A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
RU2015123817A (ru) 2012-11-22 2017-01-10 Басф Корпорейшн Пестицидные смеси
EP2922395B1 (en) 2012-11-22 2019-06-05 BASF Corporation Pesticidal mixtures
WO2014079774A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079770A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079841A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079804A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079820A1 (en) 2012-11-22 2014-05-30 Basf Se Use of anthranilamide compounds for reducing insect-vectored viral infections
WO2014079752A1 (en) 2012-11-23 2014-05-30 Basf Se Pesticidal mixtures
WO2014079813A1 (en) 2012-11-23 2014-05-30 Basf Se Pesticidal mixtures
WO2014090700A1 (en) 2012-12-14 2014-06-19 Basf Se Malononitrile compounds for controlling animal pests
CN105189489A (zh) 2012-12-27 2015-12-23 巴斯夫欧洲公司 用于防除无脊椎动物害虫的带有亚胺或亚胺衍生取代基的2-(吡啶-3-基)-5-杂芳基噻唑化合物
WO2014128136A1 (en) 2013-02-20 2014-08-28 Basf Se Anthranilamide compounds and their use as pesticides
BR112015026357A2 (pt) * 2013-04-19 2017-07-25 Basf Se compostos, composição agrícola ou veterinária, métodos para o combate ou controle das pragas, para a proteção de vegetais, para a proteção do material de propagação e para o tratamento de animais e utilização de um composto
HUE032876T2 (hu) * 2013-05-27 2017-11-28 Meiji Seika Pharma Co Ltd Gátlószerek háziméh paraziták ellen, és gátlási eljárások háziméh paraziták ellen ezek felhasználásával
BR112015031439A2 (pt) 2013-06-21 2017-07-25 Basf Se métodos para o combate ou controle das pragas, para o tratamento, prevenção e proteção de culturas de soja, para o controle e proteção do material de propagação dos vegetais de soja, para o combate ou controle das pragas e utilização de um composto de fórmula i
PL3022185T3 (pl) 2013-07-15 2018-02-28 Basf Se Związki szkodnikobójcze
WO2015028630A1 (en) * 2013-08-30 2015-03-05 Basf Se N-substituted pyridylidene compounds and derivatives for combating animal pests
JP2016531930A (ja) * 2013-09-19 2016-10-13 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Ｎ−アクリルイミノ複素環式化合物
WO2015040116A1 (en) 2013-09-19 2015-03-26 Basf Se N-acylimino heterocyclic compounds
WO2015055554A1 (de) 2013-10-14 2015-04-23 Bayer Cropscience Ag Wirkstoff für die saatgut- und bodenbehandlung
WO2015055505A1 (de) * 2013-10-14 2015-04-23 Bayer Cropscience Ag Wirkstoff zur bekämpfung von stinkwanzen
UY35772A (es) 2013-10-14 2015-05-29 Bayer Cropscience Ag Nuevos compuestos plaguicidas
WO2015055497A1 (en) 2013-10-16 2015-04-23 Basf Se Substituted pesticidal pyrazole compounds
JP6644681B2 (ja) 2013-10-18 2020-02-12 ビーエーエスエフ アグロケミカル プロダクツ ビー．ブイ． 土壌及び種子施用における殺有害生物活性カルボキサミド誘導体の使用、並びに処理方法
CN105873914B (zh) 2013-10-23 2018-10-19 拜耳作物科学股份公司 作为害虫防治剂的取代的喹喔啉衍生物
WO2015075174A1 (en) * 2013-11-22 2015-05-28 Basf Se N-acylimino heterocyclic compounds
US20160318897A1 (en) 2013-12-18 2016-11-03 Basf Se Azole compounds carrying an imine-derived substituent
JP2017502022A (ja) 2013-12-18 2017-01-19 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Ｎ−置換イミノ複素環式化合物
WO2015101622A1 (de) 2014-01-03 2015-07-09 Bayer Cropscience Ag Neue pyrazolyl-heteroarylamide als schädlingsbekämpfungsmittel
WO2015104422A1 (en) 2014-01-13 2015-07-16 Basf Se Dihydrothiophene compounds for controlling invertebrate pests
TW201612161A (en) 2014-01-20 2016-04-01 Bayer Cropscience Ag Quinoline derivatives as insecticides and acaricides
JP6398124B2 (ja) * 2014-03-10 2018-10-03 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 ２−アシルイミノピリジン誘導体の製造法
WO2015144813A1 (en) * 2014-03-27 2015-10-01 Basf Se N-acylimino heterocyclic compounds for controlling invertebrate pests
EP3126335B1 (de) 2014-04-02 2020-07-08 Bayer CropScience Aktiengesellschaft N-(1-(hetero)aryl-1h-pyrazol-4-yl)-(hetero)arylamid- derivate und ihre verwendung als schädlingsbekämpfungsmittel
EP3139743B1 (en) 2014-05-08 2018-03-14 Bayer CropScience Aktiengesellschaft Pyrazolopyridine sulfonamides as nematicides
EP3152216B1 (de) 2014-06-05 2019-07-24 Bayer CropScience Aktiengesellschaft Bicyclische verbindungen als schädlingsbekämpfungsmittel
WO2016001119A1 (de) * 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Insektizide und fungizide wirkstoffkombinationen
WO2016001121A1 (en) * 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Method for improved utilization of the production potential of transgenic plants
WO2016001129A1 (de) 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Verbesserte insektizide zusammensetzungen
WO2016001125A1 (en) * 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Active compound combinations and methods to protect the propagation material of plants
WO2016001120A1 (de) * 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Insektizide wirkstoffkombinationen
WO2016001122A1 (de) * 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Methoden zur verbesserung des pflanzenwachstums
TW201613866A (en) * 2014-07-07 2016-04-16 Bayer Cropscience Ag Process for preparing fluorinated iminopyridine compounds
TW201607938A (zh) 2014-07-15 2016-03-01 拜耳作物科學股份有限公司 作為殺蟲劑之新穎芳基三唑基吡啶類
BR112017005140A2 (pt) 2014-10-06 2018-01-23 Basf Se compostos, mistura, composição, métodos para a proteção de culturas e para o combate ou controle de praga de invertebrados, método não terapêutico para o tratamento de animais infestados ou infectados por parasitas e semente
WO2016055096A1 (en) 2014-10-07 2016-04-14 Bayer Cropscience Ag Method for treating rice seed
CN107873027A (zh) 2014-11-06 2018-04-03 巴斯夫欧洲公司 用于防治无脊椎动物害虫的3‑吡啶基杂双环化合物
AR102942A1 (es) 2014-12-11 2017-04-05 Bayer Cropscience Ag Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas
EP3081085A1 (en) 2015-04-14 2016-10-19 Bayer CropScience AG Method for improving earliness in cotton
UY36547A (es) 2015-02-05 2016-06-01 Bayer Cropscience Ag Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas
UY36548A (es) 2015-02-05 2016-06-01 Bayer Cropscience Ag Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas
WO2016124769A1 (en) 2015-02-06 2016-08-11 Basf Se Pyrazole compounds as nitrification inhibitors
TWI702212B (zh) 2015-02-09 2020-08-21 德商拜耳作物科學股份有限公司 作為除害劑之經取代的２－硫基咪唑基羧醯胺類
EP3255990B1 (en) 2015-02-11 2020-06-24 Basf Se Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide
EP3268353B1 (de) 2015-03-10 2020-09-09 Bayer Animal Health GmbH Pyrazolyl-derivate als schädlingsbekämpfungsmittel
BR112017021450B1 (pt) 2015-04-07 2021-12-28 Basf Agrochemical Products B.V. Métodos de controle de pragas, método de melhoria da saúde vegetal e semente revestida
ES2779532T3 (es) 2015-04-08 2020-08-18 Bayer Cropscience Ag Derivados de imidazo[1,2a]piridin-2-ilo como pesticidas y sus productos intermedios
WO2016174049A1 (en) 2015-04-30 2016-11-03 Bayer Animal Health Gmbh Anti-parasitic combinations including halogen-substituted compounds
AR104596A1 (es) 2015-05-12 2017-08-02 Basf Se Compuestos de tioéter como inhibidores de la nitrificación
JP2018516897A (ja) 2015-05-13 2018-06-28 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 殺虫性アリールピロリジン、これを合成する方法、および動物有害生物を制御するための薬剤としてのその使用
WO2016198613A1 (en) 2015-06-11 2016-12-15 Basf Se N-(thio)acylimino compounds
WO2016198611A1 (en) 2015-06-11 2016-12-15 Basf Se N-(thio)acylimino heterocyclic compounds
BR112018000308B1 (pt) 2015-07-06 2022-05-17 Bayer Cropscience Aktiengesellschaft Compostos heterocíclicos como pesticidas, composição, e método para controle de uma ou mais pestes
WO2017016883A1 (en) 2015-07-24 2017-02-02 Basf Se Process for preparation of cyclopentene compounds
MX2018001417A (es) 2015-08-07 2018-03-15 Bayer Cropscience Ag Derivados heterociclicos condensados sustituidos por 2-(het)-arilo como pesticidas.
MX2018004055A (es) 2015-10-02 2019-02-20 Basf Se Compuestos de imino con un sustituyente de 2-cloropirimidin-5-ilo como agentes de control de plagas.
AU2016347345B2 (en) 2015-10-26 2020-06-25 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
CA3003956A1 (en) 2015-11-30 2017-06-08 Basf Se Mixtures of cis-jasmone and bacillus amyloliquefaciens
WO2017093180A1 (de) 2015-12-01 2017-06-08 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
MX2018006749A (es) 2015-12-03 2018-08-15 Bayer Cropscience Ag Derivados de 3-(acetil)-1-[(1,3-tiazol-5-il)metil]-1h-imidazo[1,2- a]piridin-4-io-2-olato halogenados mesoionicos y compuestos relacionados como insecticidas.
JPWO2017104692A1 (ja) * 2015-12-15 2018-09-27 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 シロアリ防除剤
CN108471750B (zh) 2015-12-29 2020-11-20 明治制果药业株式会社 含有亚氨基吡啶衍生物的有害生物防除用组合物
US10647699B2 (en) 2016-02-11 2020-05-12 Bayer Cropscience Aktiengesellschaft Substituted 2-oxyimidazolylcarboxamides as pesticides
AU2017217183A1 (en) 2016-02-11 2018-08-23 Bayer Cropscience Aktiengesellschaft Substituted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents
WO2017144341A1 (de) 2016-02-23 2017-08-31 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
EP3210468A1 (de) 2016-02-26 2017-08-30 Bayer CropScience Aktiengesellschaft Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen
BR112018068034A2 (pt) 2016-03-09 2019-01-08 Basf Se compostos espiro da fórmula i, composição, composição agrícola para combater pragas animais, método de combate ou controle de pragas invertebradas, método de proteção de plantas, semente e uso dos compostos
BR112018068042A2 (pt) 2016-03-11 2019-01-08 Basf Se métodos para controlar pragas de plantas, material de propagação de planta e uso de um ou mais compostos de fórmula i
BR112018068638A2 (pt) 2016-03-15 2019-02-05 Bayer Cropscience Ag sulfonamidas substituídas para controle de pragas animais
EP3429997A1 (de) 2016-03-16 2019-01-23 Bayer CropScience Aktiengesellschaft N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel
PE20181898A1 (es) 2016-04-01 2018-12-11 Basf Se Compuestos biciclicos
WO2017174414A1 (de) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Naphthalin-derivate als schädlingsbekämpfungsmittel
JP7051703B2 (ja) 2016-04-15 2022-04-11 バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング ピラゾロピリミジン誘導体
RU2018141218A (ru) 2016-04-25 2020-05-26 Байер Кропсайенс Акциенгезельшафт Замещенные 2-алкилимидазолил-карбоксамиды в качестве средств для борьбы с вредителями
EP3241830A1 (de) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
EP3245865A1 (en) 2016-05-17 2017-11-22 Bayer CropScience Aktiengesellschaft Method for increasing yield in brassicaceae
WO2017198449A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in brassicaceae
WO2017198450A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in maize
WO2017198453A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in potato, tomato or alfalfa
WO2017198452A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in soybean
WO2017198454A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in cotton
WO2017198455A2 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in beta spp. plants
WO2017198451A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in small grain cereals such as wheat and rice
AU2017267129A1 (en) 2016-05-18 2018-11-22 Basf Se Capsules comprising benzylpropargylethers for use as nitrification inhibitors
US10653136B2 (en) 2016-07-11 2020-05-19 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
US10653135B2 (en) 2016-07-11 2020-05-19 Covestro Llc Methods for treating seeds with an aqueous composition and seeds treated therewith
US10750750B2 (en) 2016-07-11 2020-08-25 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
AU2017295745A1 (en) 2016-07-12 2019-01-31 Bayer Cropscience Aktiengesellschaft Bicyclic compounds as pest control agents
US10561145B2 (en) 2016-07-19 2020-02-18 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2018019937A1 (en) 2016-07-29 2018-02-01 Bayer Cropscience Aktiengesellschaft Formulation comprising a beneficial p. bilaii strain and talc for use in seed treatment
AR109107A1 (es) 2016-07-29 2018-10-31 Bayer Cropscience Ag Compuestos halógeno(tio)acilo sustituidos
MX2019001680A (es) 2016-08-10 2019-06-06 Bayer Cropscience Ag 2-heterociclilimidazolilcarboxamidas sustituidas como pesticidas.
KR102419244B1 (ko) 2016-08-15 2022-07-08 바이엘 크롭사이언스 악티엔게젤샤프트 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체
CN114716369A (zh) * 2016-09-16 2022-07-08 株式会社Mmag 有害生物防除剂的最佳制造方法
MX2019003136A (es) 2016-09-19 2019-07-18 Bayer Cropscience Ag Derivados de pirazolo [1,5-a]piridina y su uso como pesticidas.
ES2877814T3 (es) 2016-10-06 2021-11-17 Bayer Cropscience Ag Derivados de heterociclos bicíclicos condensados sustituidos con 2-(het)arilo como pesticidas
WO2018065288A1 (de) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz
MX2019004294A (es) 2016-10-14 2019-10-09 Pi Industries Ltd Derivados de fenilamina 4-sustituidos y su uso para proteger cultivos al combatir microorganismos fitopatogenicos indeseados.
AU2017342206B2 (en) 2016-10-14 2022-06-02 Pi Industries Ltd 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
TW201822637A (zh) 2016-11-07 2018-07-01 德商拜耳廠股份有限公司 用於控制動物害蟲的經取代磺醯胺類
NZ752550A (en) 2016-11-11 2023-03-31 Bayer Animal Health Gmbh New anthelmintic quinoline-3-carboxamide derivatives
KR20190084310A (ko) 2016-11-23 2019-07-16 바이엘 크롭사이언스 악티엔게젤샤프트 살충제로서의 2-[3-(알킬술포닐)-2H-인다졸-2-일]-3H-이미다조[4,5-b]피리딘 유도체 및 유사한 화합물
EP3400801A1 (en) 2017-05-10 2018-11-14 Bayer CropScience Aktiengesellschaft Plant health effect of purpureocillium lilacinum
WO2018108730A1 (de) 2016-12-16 2018-06-21 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
AU2017374992A1 (en) 2016-12-16 2019-06-20 Basf Se Pesticidal compounds
BR112019012269A2 (pt) 2016-12-16 2019-12-03 Bayer Ag compostos heterocíclicos como pesticidas
WO2018116072A1 (en) 2016-12-20 2018-06-28 Pi Industries Ltd. Heterocyclic compounds
WO2018116073A1 (en) 2016-12-21 2018-06-28 Pi Industries Ltd. 1, 2, 3-thiadiazole compounds and their use as crop protecting agent
EP3568395A1 (de) 2017-01-10 2019-11-20 Bayer Aktiengesellschaft Heterocyclen-derivate als schädlingsbekämpfungsmittel
TW201837036A (zh) 2017-01-10 2018-10-16 德商拜耳廠股份有限公司 作為除害劑之雜環衍生物（一）
US11051513B2 (en) 2017-01-26 2021-07-06 Mitsui Chemicals Agro, Inc. Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients
WO2018138050A1 (de) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
TW201833107A (zh) 2017-02-06 2018-09-16 德商拜耳廠股份有限公司 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物
EP3369320A1 (de) 2017-03-02 2018-09-05 Bayer CropScience Aktiengesellschaft Wirkstoff zur bekämpfung von wanzen
WO2018162312A1 (en) 2017-03-10 2018-09-13 Basf Se Spirocyclic derivatives
WO2018166855A1 (en) 2017-03-16 2018-09-20 Basf Se Heterobicyclic substituted dihydroisoxazoles
WO2018169045A1 (ja) 2017-03-17 2018-09-20 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 中気門亜目ダニ類の防除剤
KR102596592B1 (ko) 2017-03-28 2023-10-31 바스프 에스이 살충 화합물
WO2018177993A1 (de) 2017-03-31 2018-10-04 Bayer Cropscience Aktiengesellschaft Pyrazole zur bekämpfung von arthropoden
CN110475776B (zh) 2017-03-31 2024-03-19 拜耳作物科学股份公司 用于防治节肢动物的三环羧酰胺
KR102551432B1 (ko) 2017-03-31 2023-07-05 바스프 에스이 동물 해충 퇴치를 위한 피리미디늄 화합물 및 이의 혼합물
TWI793113B (zh) 2017-04-10 2023-02-21 日商三井化學Agro股份有限公司 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑
WO2018190350A1 (ja) 2017-04-10 2018-10-18 三井化学アグロ株式会社 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
UA126399C2 (uk) 2017-04-11 2022-09-28 Міцуі Кемікалз Агро, Інк. Піридони і сільськогосподарські і садові фунгіциди, які їх містять, як активні інгредієнти
EP3609887A1 (de) 2017-04-12 2020-02-19 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
WO2018192793A1 (en) 2017-04-20 2018-10-25 Basf Se Substituted rhodanine derivatives
AU2018254010B2 (en) 2017-04-20 2022-05-12 Pi Industries Ltd. Novel phenylamine compounds
EP3612530A1 (de) 2017-04-21 2020-02-26 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
CN110582503B (zh) 2017-04-24 2022-05-31 拜耳公司 作为有害物防治剂的稠合双环杂环化合物衍生物
CN110582492A (zh) 2017-04-26 2019-12-17 巴斯夫欧洲公司 作为农药的取代的琥珀酰亚胺衍生物
TWI782983B (zh) 2017-04-27 2022-11-11 德商拜耳廠股份有限公司 雜芳基苯基胺基喹啉及類似物
WO2018197401A1 (en) 2017-04-27 2018-11-01 Bayer Animal Health Gmbh New bicyclic pyrazole derivatives
BR112019022837A2 (pt) 2017-05-02 2020-05-26 Bayer Aktiengesellschaft Derivados heterocíclicos bicíclicos condensados substituídos por 2-(het)arila como agentes de controle de praga
CN110637019B (zh) 2017-05-02 2022-07-12 拜耳公司 作为有害物防治剂的2-(杂)芳基-取代的稠合双环杂环衍生物
CN110582484A (zh) 2017-05-03 2019-12-17 拜耳公司 三取代的甲硅烷基甲基苯氧基喹啉及其类似物
WO2018202715A1 (en) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Trisubstitutedsilylbenzylbenzimidazoles and analogues
BR112019023025A2 (pt) 2017-05-03 2020-06-02 Bayer Aktiengesellschaft Silil-heteroariloxiquinolinas trissubstituídas e análogos
ES2919280T3 (es) 2017-05-04 2022-07-22 Bayer Cropscience Ag Derivados de 2-{[2-(feniloximetil)piridin-5-il]oxi}-etanamina y compuestos relacionados como pesticidas, por ejemplo para la protección de plantas
WO2018202525A1 (en) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft Phenoxyethanamine derivatives for controlling pests
CN110546152B (zh) 2017-05-10 2023-09-08 巴斯夫欧洲公司 双环农药化合物
WO2018224455A1 (en) 2017-06-07 2018-12-13 Basf Se Substituted cyclopropyl derivatives
EP3636636B1 (en) 2017-06-08 2022-07-06 Mitsui Chemicals Agro, Inc. Pyridone compound and agricultural and horticultural fungicide
BR112019025331A2 (pt) 2017-06-16 2020-06-23 Basf Se Compostos da fórmula (i), composição, métodos de proteção de safras e de combate, método não terapêutico de tratamento, semente, uso dos compostos e uso de composto
EP3642203A1 (en) 2017-06-19 2020-04-29 Basf Se Substituted pyrimidinium compounds and derivatives for combating animal pests
WO2018234488A1 (en) 2017-06-23 2018-12-27 Basf Se SUBSTITUTED CYCLOPROPYL DERIVATIVES
AU2018293627B2 (en) 2017-06-30 2022-07-21 Elanco Animal Health Gmbh New azaquinoline derivatives
WO2019007887A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide und fungizide wirkstoffkombinationen
WO2019007888A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide wirkstoffkombinationen
WO2019007891A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide wirkstoffkombinationen
EP3284739A1 (de) 2017-07-19 2018-02-21 Bayer CropScience Aktiengesellschaft Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel
BR112020002348A2 (pt) 2017-08-04 2020-09-08 Bayer Animal Health Gmbh derivados de quinolina para tratamento de infecções por helmintos.
CN111629592A (zh) 2017-08-17 2020-09-04 拜耳作物科学有限合伙公司 液体肥料分散性组合物及其方法
ES2932627T3 (es) 2017-08-22 2023-01-23 Bayer Ag Derivados heterocíclicos como pesticidas
WO2019042932A1 (en) 2017-08-31 2019-03-07 Basf Se METHOD FOR CONTROLLING RICE PARASITES IN RICE
EP3453706A1 (en) 2017-09-08 2019-03-13 Basf Se Pesticidal imidazole compounds
EP3684181A1 (en) 2017-09-20 2020-07-29 Mitsui Chemicals Agro, Inc. Prolonged ectoparasite-controlling agent for animal
CN117430622A (zh) 2017-10-04 2024-01-23 拜耳公司 用作害虫防治剂的杂环化合物的衍生物
EP3694852A1 (en) 2017-10-13 2020-08-19 Basf Se Imidazolidine pyrimidinium compounds for combating animal pests
EP3473103A1 (de) 2017-10-17 2019-04-24 Bayer AG Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon
TWI784067B (zh) 2017-10-18 2022-11-21 德商拜耳廠股份有限公司 具有殺昆蟲/殺蟎性質之活性化合物組合（四）
AR113444A1 (es) 2017-10-18 2020-05-06 Bayer Ag Combinaciones de compuestos activos con propiedades insecticidas / acaricidas
EP3473100A1 (en) 2017-10-18 2019-04-24 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
BR112020007577B1 (pt) 2017-10-18 2022-06-21 Bayer Aktiengesellschaft Combinações de composto ativo sinérgicas, que apresentam propriedades inseticidas/acaricidas, seus usos, método para controlar pragas animais ou microbianas, e processo para preparar um agente de proteção de cultura
KR102625757B1 (ko) 2017-10-18 2024-01-17 바이엘 악티엔게젤샤프트 살곤충/살진드기 특성을 갖는 활성 화합물 조합물
KR102650039B1 (ko) 2017-10-18 2024-03-22 바이엘 악티엔게젤샤프트 살곤충/살진드기 특성을 갖는 활성 화합물 조합물
EP3689877A4 (en) 2017-11-03 2020-08-19 South China Agricultural University MERGED TRICYCLIC COMPOUND CONTAINING NITROGEN AND ITS USE AS AN AGROFORESTRY INSECTICIDE
EP3710432A1 (en) 2017-11-13 2020-09-23 Bayer Aktiengesellschaft Tetrazolylpropyl derivatives and their use as fungicides
CN111601802A (zh) 2017-11-28 2020-08-28 拜耳股份有限公司 作为杀虫剂的杂环化合物
WO2019121143A1 (en) 2017-12-20 2019-06-27 Basf Se Substituted cyclopropyl derivatives
BR112020012614A2 (pt) 2017-12-20 2020-11-24 Pi Industries Ltd compostos de fluoralquenil, processo de preparação e utilização
BR112020012566B1 (pt) 2017-12-21 2024-03-05 Basf Se Composto da fórmula i, composição, método de combate ou controle de pragas invertebradas, método de proteção de plantas em crescimento contra ataque ou infestação por pragas invertebradas, semente revestida, e usos de um composto da fórmula i
TW201927768A (zh) 2017-12-21 2019-07-16 德商拜耳廠股份有限公司 三取代矽基甲基雜芳氧基喹啉及類似物
WO2019145140A1 (en) 2018-01-09 2019-08-01 Basf Se Silylethynyl hetaryl compounds as nitrification inhibitors
WO2019137995A1 (en) 2018-01-11 2019-07-18 Basf Se Novel pyridazine compounds for controlling invertebrate pests
EP3305786A3 (de) 2018-01-22 2018-07-25 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2019150311A1 (en) 2018-02-02 2019-08-08 Pi Industries Ltd. 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms
EP3752492B1 (en) 2018-02-12 2022-12-21 Bayer Aktiengesellschaft Fungicidal oxadiazoles
WO2019162174A1 (de) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2019162228A1 (en) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides
EP3758491A1 (en) 2018-02-28 2021-01-06 Basf Se Use of pyrazole propargyl ethers as nitrification inhibitors
EP3758492A1 (en) 2018-02-28 2021-01-06 Basf Se Use of alkoxypyrazoles as nitrification inhibitors
IL276745B2 (en) 2018-02-28 2023-10-01 Basf Se Use of N-functional alkoxy pyrazole compounds as nitrification inhibitors
EP3765465B1 (de) 2018-03-12 2022-05-25 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2019175713A1 (en) 2018-03-14 2019-09-19 Basf Corporation New catechol molecules and their use as inhibitors to p450 related metabolic pathways
WO2019175712A1 (en) 2018-03-14 2019-09-19 Basf Corporation New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways
WO2019185413A1 (en) 2018-03-27 2019-10-03 Basf Se Pesticidal substituted cyclopropyl derivatives
WO2019197371A1 (en) 2018-04-10 2019-10-17 Bayer Aktiengesellschaft Oxadiazoline derivatives
MX2020010792A (es) 2018-04-13 2020-10-28 Bayer Ag Combinaciones de ingredientes activos con propiedades insecticidas, fungicidas y acaricidas.
WO2019197615A1 (de) 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften
UY38184A (es) 2018-04-17 2019-10-31 Bayer Ag Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas
US20210169080A1 (en) 2018-04-20 2021-06-10 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
CN112135819A (zh) 2018-04-20 2020-12-25 拜耳公司 作为杀虫剂的杂芳基-三唑与杂芳基-四唑化合物
CN108503559B (zh) * 2018-04-23 2021-10-01 上海诗丹德生物技术有限公司 辣椒碱卤代衍生物的合成及其应用
MX2020011873A (es) 2018-05-09 2021-01-20 Bayer Animal Health Gmbh Nuevos derivados de quinolina.
WO2019219529A1 (en) 2018-05-15 2019-11-21 Basf Se Mixtures comprising benzpyrimoxan and oxazosulfyl and uses and methods of applying them
WO2019224092A1 (en) 2018-05-22 2019-11-28 Basf Se Pesticidally active c15-derivatives of ginkgolides
WO2019224143A1 (de) 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
CA3104880A1 (en) 2018-06-25 2020-01-02 Bayer Cropscience Lp Seed treatment method
WO2020002189A1 (de) 2018-06-27 2020-01-02 Bayer Aktiengesellschaft Wirkstoffkombinationen
WO2020002472A1 (en) 2018-06-28 2020-01-02 Basf Se Use of alkynylthiophenes as nitrification inhibitors
CA3105411A1 (en) 2018-07-05 2020-01-09 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
ES2983787T3 (es) 2018-07-23 2024-10-24 Basf Se Uso de 2-tiazolinas sustituidas como inhibidores de la nitrificación
WO2020020765A1 (en) 2018-07-23 2020-01-30 Basf Se Use of a substituted thiazolidine compound as nitrification inhibitor
WO2020022412A1 (ja) 2018-07-25 2020-01-30 三井化学アグロ株式会社 ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤
WO2020020813A1 (en) 2018-07-25 2020-01-30 Bayer Aktiengesellschaft Fungicidal active compound combinations
WO2020020816A1 (en) 2018-07-26 2020-01-30 Bayer Aktiengesellschaft Novel triazole derivatives
CA3107207A1 (en) 2018-07-27 2020-01-30 Bayer Aktiengesellschaft Controlled release formulations for agrochemicals
US20210307322A1 (en) 2018-07-31 2021-10-07 Bayer Aktiengesellschaft Controlled release formulations with lignin for agrochemicals
AR115984A1 (es) 2018-08-17 2021-03-17 Pi Industries Ltd Compuestos de 1,2-ditiolona y sus usos
EP3613736A1 (en) 2018-08-22 2020-02-26 Basf Se Substituted glutarimide derivatives
EP3849975A1 (de) 2018-09-13 2021-07-21 Bayer Aktiengesellschaft Heterocyclen-derivate als schädlingsbekämpfungsmittel
JP2022500459A (ja) 2018-09-17 2022-01-04 バイエル・アクチエンゲゼルシヤフト 穀物中の麦角病菌の制御と菌核の低減のための殺菌剤イソフクシプラムの使用
CN111328260B (zh) * 2018-09-27 2022-06-24 株式会社Mmag 水性悬浮状农药组合物
WO2020064492A1 (en) 2018-09-28 2020-04-02 Basf Se Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof
EP3628158A1 (en) 2018-09-28 2020-04-01 Basf Se Pesticidal mixture comprising a mesoionic compound and a biopesticide
EP3628156A1 (en) 2018-09-28 2020-04-01 Basf Se Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants
EP3628157A1 (en) 2018-09-28 2020-04-01 Basf Se Method of controlling insecticide resistant insects and virus transmission to plants
WO2020070050A1 (en) 2018-10-01 2020-04-09 Bayer Aktiengesellschaft Fungicidal 5-substituted imidazol-1-yl carbinol derivatives
WO2020079173A1 (en) 2018-10-18 2020-04-23 Bayer Aktiengesellschaft Pyridylphenylaminoquinolines and analogues
CA3116626A1 (en) 2018-10-18 2020-04-23 Bayer Aktiengesellschaft Heteroarylaminoquinolines and analogues
TW202028193A (zh) 2018-10-20 2020-08-01 德商拜耳廠股份有限公司 氧雜環丁基苯氧基喹啉及類似物
EP3643711A1 (en) 2018-10-24 2020-04-29 Bayer Animal Health GmbH New anthelmintic compounds
EP3643705A1 (en) 2018-10-24 2020-04-29 Basf Se Pesticidal compounds
AR117169A1 (es) 2018-11-28 2021-07-14 Bayer Ag (tio)amidas de piridazina como compuestos fungicidas
WO2020109039A1 (en) 2018-11-28 2020-06-04 Basf Se Pesticidal compounds
EP3620052A1 (en) 2018-12-12 2020-03-11 Bayer Aktiengesellschaft Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize
AR117291A1 (es) 2018-12-14 2021-07-28 Syngenta Crop Protection Ag Compuestos heterocíclicos de cianamida con actividad pesticida
US20230031024A1 (en) 2018-12-18 2023-02-02 Basf Se Substituted pyrimidinium compounds for combating animal pests
US20220061323A1 (en) 2018-12-18 2022-03-03 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
MX2021007515A (es) 2018-12-20 2021-08-05 Bayer Ag Compuestos de heterociclil piridazina como fungicidas.
EP3669652A1 (en) 2018-12-21 2020-06-24 Bayer AG Active compound combination
TW202039477A (zh) 2018-12-21 2020-11-01 德商拜耳廠股份有限公司 作為新穎抗真菌劑之1,3,4-㗁二唑及其衍生物
EP3679792A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679789A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679793A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679790A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679791A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3696177A1 (en) 2019-02-12 2020-08-19 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2020169526A1 (en) 2019-02-18 2020-08-27 Syngenta Crop Protection Ag Pesticidally-active cyanamide heterocyclic compounds
WO2020178067A1 (en) 2019-03-01 2020-09-10 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
AR118247A1 (es) 2019-03-05 2021-09-22 Bayer Ag Combinación de compuestos activos
WO2020182929A1 (en) 2019-03-13 2020-09-17 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
US20220183293A1 (en) 2019-03-15 2022-06-16 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
US20220240508A1 (en) 2019-05-10 2022-08-04 Bayer Cropscience Lp Active compound combinations
EP3769623A1 (en) 2019-07-22 2021-01-27 Basf Se Mesoionic imidazolium compounds and derivatives for combating animal pests
BR112021019416A2 (pt) 2019-05-29 2021-12-07 Basf Se Compostos, composição, métodos de proteção de safras e de combate, controle, prevenção ou proteção contra infestações, método não terapêutico de tratamento de animais infestados, semente e uso
BR112021025700A2 (pt) 2019-06-21 2022-02-08 Bayer Ag Hidróxi-isoxazolinas e derivados das mesmas
BR112021025333A2 (pt) 2019-06-21 2022-05-24 Bayer Ag Benzilfenil hidróxi-isoxazolinas e análogos como novos agentes antifúngicos
WO2020254490A1 (en) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents
BR112021025242A2 (pt) 2019-06-21 2022-01-25 Bayer Ag Hidróxi-isoxazolinas e derivados das mesmas
EP3986888A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Thienylhydroxyisoxazolines and derivatives thereof
EP3986876A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and derivatives thereof
BR112021025305A2 (pt) 2019-06-21 2022-02-01 Bayer Ag Hidroxi-isoxazolinas e uso das mesmas como fungicidas
WO2020256091A1 (ja) 2019-06-21 2020-12-24 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 フルピリミンを含有するイネ害虫防除用固形製剤
EP3986889A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Fungicidal oxadiazoles
JP2022538262A (ja) 2019-07-03 2022-09-01 バイエル・アクチエンゲゼルシヤフト 殺菌薬としての置換されたチオフェンカルボキサミド類及びそれの誘導体
EP3766879A1 (en) 2019-07-19 2021-01-20 Basf Se Pesticidal pyrazole derivatives
TW202120490A (zh) 2019-07-30 2021-06-01 德商拜耳動物保健有限公司 新穎異喹啉衍生物
EP4068968A1 (de) 2019-09-11 2022-10-12 Bayer Aktiengesellschaft Hochwirksame formulierungen auf basis von 2-[(2;4-dichlorphenyl)-m ethyl -4,4'-dimethyl- 3-isoxazolidinone sowie vorauflaufherbiziden
CA3165263A1 (en) 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thienyloxazolones and analogues
CN118496197A (zh) 2019-12-20 2024-08-16 拜耳公司 取代的噻吩甲酰胺、噻吩甲酸及其衍生物
EP3708565A1 (en) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphenylamidines and the use thereof as fungicides
BR112022020315A2 (pt) 2020-04-09 2022-12-13 Bayer Animal Health Gmbh Novos compostos anti-helmínticos
WO2021209490A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephenylaminoquinolines as fungicides
EP4135523B1 (en) 2020-04-16 2024-09-25 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
BR112022020774A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo as mesmas
EP4135518B1 (en) 2020-04-16 2024-09-25 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
CA3180165A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
BR112022020704A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo os mesmos
JP2023538713A (ja) 2020-05-06 2023-09-11 バイエル、アクチエンゲゼルシャフト 殺真菌性化合物としてのピリジン（チオ）アミド
US20230180756A1 (en) 2020-05-12 2023-06-15 Bayer Aktiengesellschaft Triazine and pyrimidine (thio)amides as fungicidal compounds
WO2021233861A1 (en) 2020-05-19 2021-11-25 Bayer Aktiengesellschaft Azabicyclic(thio)amides as fungicidal compounds
CN115803320A (zh) 2020-06-04 2023-03-14 拜耳公司 作为新的杀真菌剂的杂环基嘧啶类和杂环基三嗪类
WO2021249995A1 (en) 2020-06-10 2021-12-16 Bayer Aktiengesellschaft Azabicyclyl-substituted heterocycles as fungicides
KR20230026388A (ko) 2020-06-18 2023-02-24 바이엘 악티엔게젤샤프트 작물 보호를 위한 살진균제로서의 3-(피리다진-4-일)-5,6-디히드로-4h-1,2,4-옥사디아진 유도체
BR112022025692A2 (pt) 2020-06-19 2023-02-28 Bayer Ag 1,3,4-oxadiazóis e seus derivados como fungicidas
UY39276A (es) 2020-06-19 2022-01-31 Bayer Ag Uso de compuestos de 1,3,4–oxadiazol–2–ilpirimidina para controlar microorganismos fitopatógenos, métodos de uso y composiciones.
WO2021255089A1 (en) 2020-06-19 2021-12-23 Bayer Aktiengesellschaft 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides
UY39275A (es) 2020-06-19 2022-01-31 Bayer Ag 1,3,4-oxadiazol pirimidinas como fungicidas, procesos e intermediarios para su preparación, métodos de uso y usos de los mismos
WO2022058327A1 (en) 2020-09-15 2022-03-24 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
EP3915371A1 (en) 2020-11-04 2021-12-01 Bayer AG Active compound combinations and fungicide compositions comprising those
EP3915971A1 (en) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phenyl-s(o)n-phenylamidines and the use thereof as fungicides
WO2022129196A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft Heterobicycle substituted 1,2,4-oxadiazoles as fungicides
WO2022129188A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazol-3-yl pyrimidines as fungicides
WO2022129190A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides
US20240122092A1 (en) 2021-01-28 2024-04-18 Specialty Operations France Method for treating rice seed with improved retention of agrochemical, micronutrient and colorant
AR124796A1 (es) 2021-02-02 2023-05-03 Basf Se Acción sinérgica de dcd y alcoxipirazoles como inhibidores de la nitrificación
WO2022200364A1 (en) 2021-03-25 2022-09-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
CA3219022A1 (en) 2021-05-21 2022-11-24 Barbara Nave Use of ethynylpyridine compounds as nitrification inhibitors
US20240270658A1 (en) 2021-05-21 2024-08-15 Basf Se Use of an N-Functionalized Alkoxy Pyrazole Compound as Nitrification Inhibitor
AU2022296764A1 (en) 2021-06-21 2024-01-04 Basf Se Metal-organic frameworks with pyrazole-based building blocks
WO2022268815A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2022268813A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
EP4148052A1 (en) 2021-09-09 2023-03-15 Bayer Animal Health GmbH New quinoline derivatives
WO2023078915A1 (en) 2021-11-03 2023-05-11 Bayer Aktiengesellschaft Bis(hetero)aryl thioether (thio)amides as fungicidal compounds
WO2023092050A1 (en) 2021-11-20 2023-05-25 Bayer Cropscience Lp Beneficial combinations with recombinant bacillus cells expressing a serine protease
WO2023099445A1 (en) 2021-11-30 2023-06-08 Bayer Aktiengesellschaft Bis(hetero)aryl thioether oxadiazines as fungicidal compounds
CA3242421A1 (en) 2021-12-15 2023-06-22 Bayer Aktiengesellschaft Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis
AU2023258006A1 (en) 2022-04-18 2024-10-31 Basf Corporation High-load agricultural formulations and methods of making same
WO2023203066A1 (en) 2022-04-21 2023-10-26 Basf Se Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers
WO2024028243A1 (en) 2022-08-02 2024-02-08 Basf Se Pyrazolo pesticidal compounds
IT202200024963A1 (it) * 2022-12-05 2024-06-05 Angelini Pharma S P A Composti attivatori dei canali potassio Kv7.2/Kv7.3
CN115960043A (zh) * 2023-01-30 2023-04-14 江西新龙生物科技股份有限公司 一种新烟碱杀虫剂及其合成方法
WO2024213752A1 (en) 2023-04-14 2024-10-17 Elanco Animal Health Gmbh Long-term prevention and/or treatment of a disease by slo-1 inhibitors

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1285390A (en) * 1969-12-23 1972-08-16 Pharmacia Ab Improvements in the n-alkylation of acylated amino compounds
US3867447A (en) 1972-08-25 1975-02-18 Du Pont Hydroxyguanidine O-carbamates
AU5950573A (en) 1972-08-25 1975-02-27 Du Pont Mono- and disubstituted hydroxyguanidines
US4203988A (en) * 1975-11-12 1980-05-20 Merck & Co., Inc. Pyridinyl ureas and pharmaceutical use
US4206141A (en) * 1978-12-15 1980-06-03 Stauffer Chemical Company Process for preparation of di-substituted cyanamides using quaternary salt catalysis
JPH07121909B2 (ja) 1986-09-10 1995-12-25 日本バイエルアグロケム株式会社 新規複素環式化合物及び殺虫剤
DE3639877A1 (de) * 1986-11-21 1988-05-26 Bayer Ag Hetarylalkyl substituierte 5- und 6-ringheterocyclen
JPS63227552A (ja) * 1987-03-13 1988-09-21 Shionogi & Co Ltd ２−フルオロエチル誘導体、その製造法およびそれを有効成分とする有害生物防除剤
JP2859301B2 (ja) * 1989-07-08 1999-02-17 武田薬品工業株式会社 農園芸用殺虫組成物
HU207047B (en) * 1989-11-07 1993-03-01 Richter Gedeon Vegyeszet Process for producing new pyridine derivatives and pharmaceutical copositions comprising same
DE4021439A1 (de) * 1989-12-14 1991-06-20 Bayer Ag 2-iminopyridin-derivate
JPH0578323A (ja) 1991-03-11 1993-03-30 Nippon Soda Co Ltd 新規なヘテロ環化合物、その製造方法及び殺虫剤
US5559108A (en) * 1994-09-02 1996-09-24 Bristol-Myers Squibb Company Cephalosporin derivatives
US5804686A (en) * 1996-01-19 1998-09-08 Neurogen Corporation fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
ATE433442T1 (de) * 1997-04-07 2009-06-15 Nihon Nohyaku Co Ltd Pyrazolderivate, verfahren zu ihrer herstellung, zwischenprodukte und schädlingsbekämpfungsmittel, das diese als aktiven bestandteil enthält
JP3190859B2 (ja) 1997-07-29 2001-07-23 松下電器産業株式会社 Ｃｄｍａ無線送信装置及びｃｄｍａ無線受信装置
JP2002520384A (ja) * 1998-07-16 2002-07-09 アベンテイス・アグリカルチヤー・リミテツド アリールビニルエーテル誘導体およびそれらの除草剤としての使用
DE10063486A1 (de) * 2000-12-20 2002-07-04 Bayer Ag Dichlorpyridylmethylamide
JP2003026661A (ja) 2001-06-27 2003-01-29 Sinon Corp 複素環化合物
JP2005225860A (ja) * 2003-11-11 2005-08-25 Ishihara Sangyo Kaisha Ltd ビフェニル誘導体又はその塩、それらを有効成分として含有する有害生物防除剤
AR046698A1 (es) 2003-11-11 2005-12-21 Ishihara Sangyo Kaisha Derivado bifenilo o su sal, y pesticida que lo contienen como un ingrediente activo
DE102004018953A1 (de) 2004-04-20 2005-11-17 Bayer Cropscience Gmbh 4-Halogenalkylpyridin-3-sulfonsäureamide, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
DE102004041529A1 (de) 2004-08-27 2006-03-02 Bayer Cropscience Gmbh Herbizid-Kombinationen mit speziellen Ketoenolen
US8604055B2 (en) * 2004-12-31 2013-12-10 Dr. Reddy's Laboratories Ltd. Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
WO2006138148A1 (en) * 2005-06-13 2006-12-28 Bayer Cropscience Ag Pesticidal 5-bis(methoxymethyl)aminopyrazole derivatives
WO2007105814A1 (ja) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. 置換イソキサゾリン化合物及び有害生物防除剤
ZA200810739B (en) 2006-06-20 2010-03-31 Ishihara Sangyo Kaisha Pesticide containing novel pyridyl-methanamine derivative or its salt
JP5078323B2 (ja) 2006-11-20 2012-11-21 株式会社カプコン ゲーム装置、そのゲーム装置を実現するためのプログラム及び記録媒体
JP4985025B2 (ja) 2007-03-28 2012-07-25 凸版印刷株式会社 マイクロニードルチップ集合体、マイクロニードルチップ、医療器具、マイクロニードルチップ集合体製造方法およびマイクロニードルチップ製造方法
JP2008260691A (ja) * 2007-04-10 2008-10-30 Bayer Cropscience Ag 殺虫性アリールイソオキサゾリン誘導体
JP2008266230A (ja) * 2007-04-23 2008-11-06 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JPWO2009038064A1 (ja) * 2007-09-19 2011-01-06 株式会社医薬分子設計研究所 Ｉ型１１βヒドロキシステロイド脱水素酵素阻害活性を有する複素環誘導体
US7683064B2 (en) 2008-02-05 2010-03-23 Roche Palo Alto Llc Inhibitors of Bruton's tyrosine kinase
KR20100113598A (ko) * 2008-02-07 2010-10-21 바이엘 크롭사이언스 아게 살충성 아릴피롤린
JP2010138082A (ja) * 2008-12-09 2010-06-24 Nippon Soda Co Ltd 環状アミン化合物またはその塩、並びに有害生物防除剤
CN102892290B (zh) * 2010-08-31 2016-02-03 明治制果药业株式会社 有害生物防除剂
EP2749555B1 (en) * 2011-08-26 2018-11-14 Meiji Seika Pharma Co., Ltd. Method for producing pest controlling agent
BR112014020831B8 (pt) * 2012-02-29 2022-11-22 Meiji Seika Pharma Co Ltd Composição de controle de peste incluindo derivado de iminopiridina, seu uso e método para pro-teger plantas úteis de pestes

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