US 6,475,955 B2Granted

Pyridazinone derivatives

AssigneeSumitomo Chemical Company, Limited

InventorTakashi Komori

Life of this patent

Estimating the term…

Abstract

This invention provides pyridazinone derivatives encompassed by the following the formula: wherein, R1, R2, R3, R4, R5 and R7 represent a hydrogen atom and the like, and R6 represents a C1-C3 alkyl and the like. The pyridazinone derivatives have excellent herbicidal activity, therefore, they can be used as an active ingredient for herbicidal compositions and can be utilized in herbicidal method, which are also described.

Claims11

Dependent claims

A pyridazinone derivative encompassed by the following formula:

wherein, R1 represents hydrogen, halogen, C1-C3 alkyl or C1-C3 haloalkyl;
R2 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, NO2 or CN;
R3 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C3 alkoxy C1-C3 alkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, C(R121)═C(R14)(R15), NO2 or CN;
R4 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C3 alkoxy C1-C3 alkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, C(R121)═C(R14)(R15), C(R16)═NOR17, NO2 or CN;
R5 represents hydrogen, halogen or C1-C3 alkyl;
R6 represents C1-C3 alkyl or C1-C3 haloalkyl;
R7 represents hydrogen, halogen, or C1-C3 alkyl;
and in which;
R8represents hydrogen, a C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl, C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, SO2R20, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R9 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R10 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, SR18, SOR19, SO2R20, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R11 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 alkenyl, C3-C10 haloalkenyl,C3-C10 alkynyl, C3-C10 haloalkynyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl, N(R21)(R22), N═C(R21)(R22), C1-C5 alkoxycarbonyl C1-C3 alkyl or C1-C5 haloalkoxycarbonyl C1-C3 alkyl;
R12 represents hydrogen, chlorine, C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyclohaloalkyl or N(R23)(R24);
R13 represents chlorine, C1-C10 alkyl, C1-C10 haloalkyl, N(R25)(R26) or OR27;
R14 represents hydrogen, halogen or C1-C3 alkyl;
R15 represents hydrogen, COOR28, cyano or C1-C5 alkyl;
R16 represents hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C5 cycloalkyl or C3-C5 cyclohaloalkyl;
R17 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyclohaloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C5 alkenyl, C3-C5 haloalkenyl, C3-C5 alkynyl, C3-C5 haloalkynyl, C1-C5 alkoxycarbonyl C1-C3 alkyl, C1-C5 haloalkoxycarbonyl C1-C3 alkyl, phenyl that may have a substituent or substituents or phenyl C1-C3 alkyl that may have a substituent or substituents;
R18 represents C1-C10 alkyl, C1-C10 haloalkyl or phenyl that may have a substituent or substituents;
R19 represents C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R20 represents C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R21 represents hydrogen or C1-C5 alkyl;
R22 represents hydrogen, C1-C5 alkyl, C1-C8 haloalkyl or phenyl that may have a substituent or substituents;
R23 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R24 represents hydrogen, C1-C10 alkyl or C1-C10 haloalkyl;
R25 represents hydrogen, C1-C5 alkyl or C1-C5 haloalkyl;
R26 represents hydrogen, C1-C10 alkyl or C1-C10 haloalkyl;
R27 represents hydrogen, C1-C10 alkyl;
R28 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R41 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 alkenyl and C3-C8 alkynyl,
R42 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 alkenyl and C3-C8 alkynyl, and
R121 represents hydrogen, chlorine C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 cycloalkyl or C3-C6 cyclohaloalkyl.

29 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/732,901Filed 11 Dec 2000 · division
Priority: JP 10-07903126 Mar 1998
Published: US 2002/0026048 A128 Feb 2002
Granted: 5 Nov 2002
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 237/14
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines
C07D 237/26
Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings: condensed with carbocyclic rings or ring systems
C07D 237/30
Condensed with carbocyclic rings or ring systems: phthalazines

Family

Application09/275,266Parent of this division · filed 23 Mar 1999
US 2002/0026048 A1Pre-grant publication · published 28 Feb 2002
US 6,187,920 B1Parent of this division
US 6,475,955 B2This patent

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

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Abstract

A pyridazinone derivative encompassed by the following formula:

wherein, R1 represents hydrogen, halogen, C1-C3 alkyl or C1-C3 haloalkyl;
R2 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, NO2 or CN;
R3 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C3 alkoxy C1-C3 alkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, C(R121)═C(R14)(R15), NO2 or CN;
R4 represents hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C3 alkoxy C1-C3 alkyl, OR8, SR9, NHR10, COOR11, COR12, SO2R13, C(R121)═C(R14)(R15), C(R16)═NOR17, NO2 or CN;
R5 represents hydrogen, halogen or C1-C3 alkyl;
R6 represents C1-C3 alkyl or C1-C3 haloalkyl;
R7 represents hydrogen, halogen, or C1-C3 alkyl;
and in which;
R8represents hydrogen, a C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl, C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, SO2R20, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R9 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R10 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl, C3-C10 cycloalkenyl, C3-C10 cyclohaloalkenyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C10 cycloalkenyl C1-C3 alkyl, C3-C10cyclohaloalkenyl C1-C3 alkyl, C1-C5 alkylcarbonyl, C1-C5 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 cyclohaloalkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 haloalkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 haloalkoxycarbonyl, C3-C10 cycloalkoxycarbonyl, C3-C10 cyclohaloalkoxycarbonyl, C1-C10 alkoxycarbonyl C1-C5 alkyl, C1-C10 haloalkoxycarbonyl C1-C5 alkyl, C3-C10 cycloalkoxycarbonyl C1-C5 alkyl, C3-C10 cyclohaloalkoxycarbonyl C1-C5 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 haloalkylthio C1-C6 alkyl, cyano C1-C4 alkyl, phenyl that may have a substituent or substituents, phenyl C1-C3 alkyl that may have a substituent or substituents, phenylcarbonyl that may have a substituent or substituents, SR18, SOR19, SO2R20, CH2C(═O)CO2R41, CH(CH3)C(═O)CO2R41, CH2C(═NOR42)CO2R41 or CH(CH3)C(═NOR42)CO2R41;
R11 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 alkenyl, C3-C10 haloalkenyl,C3-C10 alkynyl, C3-C10 haloalkynyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl, N(R21)(R22), N═C(R21)(R22), C1-C5 alkoxycarbonyl C1-C3 alkyl or C1-C5 haloalkoxycarbonyl C1-C3 alkyl;
R12 represents hydrogen, chlorine, C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyclohaloalkyl or N(R23)(R24);
R13 represents chlorine, C1-C10 alkyl, C1-C10 haloalkyl, N(R25)(R26) or OR27;
R14 represents hydrogen, halogen or C1-C3 alkyl;
R15 represents hydrogen, COOR28, cyano or C1-C5 alkyl;
R16 represents hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C5 cycloalkyl or C3-C5 cyclohaloalkyl;
R17 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C6 cycloalkyl, C3-C6 cyclohaloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 cyclohaloalkyl C1-C3 alkyl, C3-C5 alkenyl, C3-C5 haloalkenyl, C3-C5 alkynyl, C3-C5 haloalkynyl, C1-C5 alkoxycarbonyl C1-C3 alkyl, C1-C5 haloalkoxycarbonyl C1-C3 alkyl, phenyl that may have a substituent or substituents or phenyl C1-C3 alkyl that may have a substituent or substituents;
R18 represents C1-C10 alkyl, C1-C10 haloalkyl or phenyl that may have a substituent or substituents;
R19 represents C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R20 represents C1-C10 alkyl, C1-C10 haloalkyl, C3-C8 cycloalkyl, C3-C8 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R21 represents hydrogen or C1-C5 alkyl;
R22 represents hydrogen, C1-C5 alkyl, C1-C8 haloalkyl or phenyl that may have a substituent or substituents;
R23 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R24 represents hydrogen, C1-C10 alkyl or C1-C10 haloalkyl;
R25 represents hydrogen, C1-C5 alkyl or C1-C5 haloalkyl;
R26 represents hydrogen, C1-C10 alkyl or C1-C10 haloalkyl;
R27 represents hydrogen, C1-C10 alkyl;
R28 represents hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cyclohaloalkyl or phenyl that may have a substituent or substituents;
R41 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 alkenyl and C3-C8 alkynyl,
R42 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 alkenyl and C3-C8 alkynyl, and
R121 represents hydrogen, chlorine C1-C5 alkyl, C1-C5 haloalkyl, C3-C6 cycloalkyl or C3-C6 cyclohaloalkyl.

29 more elements

Facts

Application

09/732,901Filed 11 Dec 2000 · division

Priority

JP 10-07903126 Mar 1998

Published

US 2002/0026048 A128 Feb 2002

Granted

5 Nov 2002

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 237/14
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A01N 43/58
Having rings with two nitrogen atoms as the only ring hetero atoms: 1,2-Diazines; Hydrogenated 1,2-diazines
C07D 237/26
Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings: condensed with carbocyclic rings or ring systems
C07D 237/30
Condensed with carbocyclic rings or ring systems: phthalazines