EP0169051A2
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EP
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Pyridazinylurea compounds
Assignee: Eli Lilly and Co
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Filing: 1985-07-15
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Granted: —
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Expires: 2005-07-15
Abstract
Abstract This invention describes novel pyridazinylurea compounds, which are useful as herbicides.
Inventors
- 👤 Riaz Fazal Abdulla
- 👤 Jack Geno Samaritoni
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 04:00
CPC Classifications
A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C; C07; C07D; C07D237/00; C07D237/02; C07D237/06; C07D237/10; C07D237/20; C07D237/22
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
175 words
A method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (II) wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkox y , C 2 -C 6 alkenyl, (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, di(C 1 -C 4 alkoxy)Cl-C6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C6 alkyl, or (C I - C 6 acyloxy)C 1 -C 6 alkyl; or together with the nitrogen form a heterocyclic ring containing 5 or 6 ring atoms, and m is an integer from 0 to 3.
Claim 2
Independent Claim
175 words
A method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (II) wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkox y , C 2 -C 6 alkenyl, (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, di(C 1 -C 4 alkoxy)Cl-C6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C6 alkyl, or (C I - C 6 acyloxy)C 1 -C 6 alkyl; or together with the nitrogen form a heterocyclic ring containing 5 or 6 ring atoms, and m is an integer from 0 to 3.
Claim 3
Dependent Claim
170 words
A compound of the formula (II) as defined in Claim 1, wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently C 1 -C 6 alkyl, C 1 -C 6 alkox y, C 2 -C 6 alkenyl, (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, di(C 1 -C 4 alkoxy)C 1 -C 6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C 6 alkyl, or (C 1 -C 6 acylox y )-C 1 -C 6 alkyl; or together with the nitrogen forms a piperidine, morpholine, or pyrrolidine group, and m is an integer from 1 to 3; provided that not more than one of R 3 and R 4 is C 1 -C 6 alkyl.
Claim 4
Dependent Claim
60 words
The compound of Claim 2 wherein R 1 is halo or C 1 -C 4 alkyl; R 2 is hydrogen; R 3 and R 4 are independently C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C2-C4 alkenyl, hydroxy(C 1 -C 4 alkyl) or (C 1 -C 6 acyloxy)C 1 -C 6 alkyl; and m is 1 or 2.
Claim 5
Dependent Claim
1 words
N'-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methoxy-N-methylurea.
Claim 6
Dependent Claim
1 words
N'-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methoxy-N-methylurea.
Claim 7
Dependent Claim
1 words
N-[2-(Acetyloxy)ethyl]-N'-[6-chloro-5-(l,l-dimethylethyl)-3-pyridazinyl]-N-methylurea.
Claim 8
Dependent Claim
1 words
N-[2-(Acetyloxy)ethyl]-N'-[6-chloro-5-(l,l-dimethylethyl)-3-pyridazinyl]-N-methylurea.
Claim 9
Dependent Claim
1 words
N'-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-(2-hydroxyethyl)-N-methylurea.
Claim 10
Dependent Claim
1 words
N'-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-(2-hydroxyethyl)-N-methylurea.
Claim 11
Dependent Claim
30 words
A herbicidal formulation which comprises as an active ingredient a compound as claimed in any one of claims 2 to 6 associated with one or more non- phytotoxic carriers therefor.
Claim 12
Dependent Claim
79 words
A process for preparing a compound of formula II as claimed in any one of claims 2 to 6, which comprises: (A) reacting a carbamate of formula: with an amine of formula HN R 3 R 4 ; (B) reacting an aminopyridazine of formula with an isocyanate of formula R 4 NCO; or a carbamoyl chloride of formula R 3 R 4 NCOC1 (C) reacting a compound of formula with an amine of formula NHR 3 R 4 .
Claim 13
Independent Claim
176 words
A method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (II) wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alk oxy, C2 -C 6 alkenyl, (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, di(C 1 -C 4 alkoxy)C 1 -C 6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C 6 alkyl, or (C 1 -C 6 acyloxy)C 1 -C 6 alkyl; or together with the nitrogen form a heterocyclic ring containing 5 or 6 ring atoms, and m is an integer from 0 to 3.
Claim 14
Independent Claim
176 words
A method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (II) wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alk oxy, C2 -C 6 alkenyl, (C 1 -C 6 alkoxy)C 1 -C 6 alkyl, di(C 1 -C 4 alkoxy)C 1 -C 6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C 6 alkyl, or (C 1 -C 6 acyloxy)C 1 -C 6 alkyl; or together with the nitrogen form a heterocyclic ring containing 5 or 6 ring atoms, and m is an integer from 0 to 3.
Claim 15
Dependent Claim
180 words
A herbicidal formulation which comprises as an active ingredient a compound of the formula (II) as defined in Claim 1, wherein R 1 is halo, trifluoromethyl, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, (C 1 -C 3 alkyl)C 3 -C 6 cycloalkyl, (C 1 -C 3 alkoxy)C 1 -C 8 alkyl, adamantyl, phenoxy, phenyl, or halo-substituted phenyl; R 2 is hydrogen, C 1 -C 6 alkyl, or C 2 -C 6 alkenyl; R 3 and R 4 are independently C 1 -C 6 alkyl, C 1 -C 6 alkox y , C 2 -C 6 alkenyl, (C 1 -C 6 alkoxy)Cl-C6 alkyl, di(C 1 -C 4 alkoxy)C1-C6 alkyl, (hydroxy)C 1 -C 6 alkyl, phenyl, benzyl, (carboxy)C 1 -C 6 alkyl, or (C 1 -C 6 acylox y )-C 1 -C 6 alkyl; or together with the nitrogen forms a piperidine, morpholine, or pyrrolidine group, and m is an integer from 1 to 3; provided that not more than one of R 3 and R 4 is C 1 -C 6 alkyl, associated with one or more-agriculturally-acceptable carriers.
Claim 16
Dependent Claim
65 words
The formulation of Claim 2 wherein R 1 is halo or C 1 -C 4 alkyl; R 2 is hydrogen; R 3 and R 4 are independently C 1 -C 3 alkyl, C 1 -C 3 alkox y , C 2 -C 4 alkenyl, hydroxy(C 1 -C 4 alkyl) or (C 1 -C 6 acyloxy)C 1 -C 6 alkyl; and m is 1 or 2.
Claim 17
Dependent Claim
11 words
The formulation of claim 2 wherein the active ingredient is N'-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methoxy-N-methylurea.
Claim 18
Dependent Claim
11 words
The formulation of claim 2 wherein the active ingredient is N-[2-(acetyloxy)ethyl]-N'-[6-chloro-5-(l,1-dimethylethyl)-3-pyridazinyl]-N-methylurea.
Claim 19
Dependent Claim
11 words
The formulation of claim 2 wherein the active ingredient is N'-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-(2-hydroxyethyl)-N-methylurea.
Claim 20
Dependent Claim
76 words
A process for preparing a compound of formula II as defined in any one of claims 2 to 6, which comprises: (A) reacting a carbamate of formula: with an amine of formula HNR 3 R 4 ; (B) reacting an aminopyridazine of formula with an isocyanate of formula R 4 NCO; or a carbamoyl chloride of formula R 3 R 4 NCOC1 (C) reacting a compound of formula with an amine of formula NHR R .
References Cited (Backward Citations)
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