US 12,180,187 B2Granted

1-phenyl-5-azinylpyrazolyl-3-oxyalkyl acids and their use for controlling unwanted plant growth

AssigneeBayer Aktiengesellschaft

InventorsMichael Gerhard Hoffmann, Estella Buscato Arsequell, Harald Jakobi, Thomas Mueller, Erin Nicole Smith, Elisabeth Asmus, Anu Bheemaiah Machettira, Elmar Gatzweiler, Christopher Hugh Rosinger, Dirk Schmutzler

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Abstract

What are described are compounds of the general formula (I) and agrochemically acceptable salts thereof and their preparation and their use in the crop protection sector.

Claims20

Dependent claims

A Compound of formula (I)

And/or an agrochemically acceptable salt thereof, where
A is selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10;
where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nNR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of hydrogen, halogen, cyano, nitro, OR5, S(O)nNR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl;
and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO;
and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
and
NH2;
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6;
and
s is 0, 1 or 2.

62 more elements

A compound of formula (II) and/or salt thereof

where,
A is selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10;
where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of
hydrogen, halogen, cyano, nitro, OR5, S(O)nR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono-to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl;
and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO;
and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
and
NH2;
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6;
and
s is 0, 1 or 2.

63 more elements

A process for preparing a compound of formula (VIII) where A is

selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10;
where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of
hydrogen, halogen, cyano, nitro, OR5, S(O)nR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono-to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl;
and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO;
and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
and
NH2:
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6;
and
s is 0, 1 or 2,
comprising a reaction of an azine-A-substituted propynoic acid of formula (VI)
with a compound of formula (VII)
in a solvent
in the presence of an amide coupling reagent.

66 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/615,786Filed 29 May 2020
Priority: EP 191779003 Jun 2019
Published: US 2022/0235036 A128 Jul 2022
Granted: 31 Dec 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A01N 43/54
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,3-Diazines; Hydrogenated 1,3-diazines
A01N 43/56
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazoles; Hydrogenated 1,2-diazoles
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines

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US 2022/0235036 A1Pre-grant publication · published 28 Jul 2022
US 12,180,187 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

What are described are compounds of the general formula (I) and agrochemically acceptable salts thereof and their preparation and their use in the crop protection sector.

A Compound of formula (I)

And/or an agrochemically acceptable salt thereof, where
A is selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10;
where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nNR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of hydrogen, halogen, cyano, nitro, OR5, S(O)nNR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl;
and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO;
and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
and
NH2;
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6;
and
s is 0, 1 or 2.

62 more elements

Facts

Application

17/615,786Filed 29 May 2020

Priority

EP 191779003 Jun 2019

Published

US 2022/0235036 A128 Jul 2022

Granted

31 Dec 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A01N 43/54
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,3-Diazines; Hydrogenated 1,3-diazines
A01N 43/56
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazoles; Hydrogenated 1,2-diazoles
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines