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N,N'-diphenyl-N-(N"-alkylcarbamoyl)formamidines

Assignee: Sandoz AG
•
Filing: 1973-02-23
•
Granted: 1976-06-29
•
Expires: 1993-02-23
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Abstract

Abstract The present invention concerns novel N,N'-diphenyl-N-(N''-alkylcarbamoyl)formamidine derivatives of the formula: Ar1-N=CH-N-Ar2 ¦ ¦R1 CO-N ANGLE R2 wherein R1 is hydrogen or alkyl, R2 is alkyl and Ar1 and Ar2 are each phenyl or a substituted phenyl, which compounds are useful as herbicides.

Inventors

  • 👤 Karl Seckinger
  • 👤 Fritz Reisser

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 20:53
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/46; C07C275/48; C07C275/56

Claims Analysis

Total Claims: 38
Claim 1
Independent Claim 116 words
A compound of the formula: ##EQU10## wherein R 1 is hydrogen or alkyl of 1 to 4 carbon atoms, R 2 is alkyl of 1 to 4 carbon atoms, and either Ar 1 and Ar 2 are the same, and are each phenyl or a substituted phenyl group selected from ##SPC9## wherein R 3 is chlorine, bromine, methyl or methoxy, and R 4 is chlorine, bromine, methyl, methoxy or trifluoromethyl, or Ar 2 is phenyl and Ar 1 is a substituted phenyl group selected from ##SPC10## wherein R 3 ' is chlorine or methyl and R 4 ' is chlorine, methyl or trifluoromethyl, with the proviso that Ar 1 and Ar 2 are other than ##SPC11##
Claim 2
Dependent Claim 116 words
A compound of the formula: ##EQU10## wherein R 1 is hydrogen or alkyl of 1 to 4 carbon atoms, R 2 is alkyl of 1 to 4 carbon atoms, and either Ar 1 and Ar 2 are the same, and are each phenyl or a substituted phenyl group selected from ##SPC9## wherein R 3 is chlorine, bromine, methyl or methoxy, and R 4 is chlorine, bromine, methyl, methoxy or trifluoromethyl, or Ar 2 is phenyl and Ar 1 is a substituted phenyl group selected from ##SPC10## wherein R 3 ' is chlorine or methyl and R 4 ' is chlorine, methyl or trifluoromethyl, with the proviso that Ar 1 and Ar 2 are other than ##SPC11##
Claim 3
Dependent Claim 10 words
A compound of claim 1, wherein R 1 is hydrogen.
Claim 4
Dependent Claim 8 words
The compound of claim 2, which is N,N'-diphenyl-N-(N"-methylcarbamoyl)formamidine.
Claim 5
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-bromophenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 6
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-trifluoromethylphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 7
Dependent Claim 8 words
The compound of claim 2, which is N,N'-(4-bromophenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 8
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-chloro-4-methylphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 9
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-chlorophenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 10
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(4-methylphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 11
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-methoxyphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 12
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-methylphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 13
Dependent Claim 8 words
The compound of claim 2, which is N,N'-di-(3-chloro-4-methoxyphenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 14
Dependent Claim 8 words
The compound of claim 2, which is N-phenyl-N-(N"-methylcarbamoyl)-N'-(4-methylphenyl)formamidine.
Claim 15
Dependent Claim 8 words
The compound of claim 2, which is N-phenyl-N-(N"-methylcarbamoyl)-N'-(4-chlorophenyl)formamidine.
Claim 16
Dependent Claim 8 words
The compound of claim 2, which is N-phenyl-N-(N"-methylcarbamoyl)-N'-(3,4-dimethylphenyl)formamidine.
Claim 17
Dependent Claim 8 words
The compound of claim 2, which is N-phenyl-N-(N"-methylcarbamoyl)-N'-(3,4-dichlorophenyl)formamidine.
Claim 18
Dependent Claim 8 words
The compound of claim 2, which is N-phenyl-N-(N"-methylcarbamoyl)-N'-(3-trifluoromethylphenyl)formamidine.
Claim 19
Dependent Claim 29 words
A compound of claim 2, wherein R 2 is methyl and Ar 1 and Ar 2 are the same and are each a substituted phenyl group selected from ##SPC12##
Claim 20
Dependent Claim 8 words
The compound of claim 18, which is N,N'-di-(4-chlorophenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 21
Dependent Claim 8 words
The compound of claim 18, which is N,N'-di-(3-dichlorophenyl)-N-(N"-methylcarbamoyl)formamidine.
Claim 22
Dependent Claim 47 words
A compound of claim 1, wherein R 1 and R 2 are each methyl and Ar 1 and Ar 2 are the same and are each a substituted phenyl group selected from ##SPC13## wherein R 3 " and R 4 " are each chlorine, bromine or methyl.
Claim 23
Dependent Claim 8 words
The compound of claim 21, which is N,N'-di-(4-bromophenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 24
Dependent Claim 8 words
The compound of claim 21, which is N,N'-di-(3-chlorophenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 25
Dependent Claim 8 words
The compound of claim 21, which is N,N'-di-(4-chlorophenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 26
Dependent Claim 8 words
The compound of claim 21, which is N,N-di-(4-methylphenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 27
Dependent Claim 8 words
The compound of claim 21, which is N,N'-di-(3-methylphenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 28
Dependent Claim 54 words
A compound of claim 1, wherein R 1 is alkyl of 1 to 4 carbon atoms and Ar 1 and Ar 2 are the same and are each phenyl or a substituted phenyl group selected from ##SPC14## wherein R 3 IV is chlorine or methoxy and R 4 IV is chlorine, methoxy or trifluoromethyl.
Claim 29
Dependent Claim 8 words
The compound of claim 27, which is N,N'-diphenyl-N-(N"-methylcarbamoyl)formamidine.
Claim 30
Dependent Claim 8 words
The compound of claim 27, which is N,N'-di-(3,4-dichlorophenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 31
Dependent Claim 8 words
The compound of claim 27, which is N,N'-di-(4-methylphenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 32
Dependent Claim 8 words
The compound of claim 27, which is N,N'-di-(3-methoxyphenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 33
Dependent Claim 8 words
The compound of claim 27, which is N,N'-di-(3-chloro-4-methoxyphenyl)-N-(N"-dimethylcarbamoyl)formamidine.
Claim 34
Dependent Claim 47 words
A compound of claim 1, wherein R 1 is alkyl of 1 to 4 carbon atoms, Ar 2 is phenyl and Ar 1 is a substituted phenyl group selected from ##SPC15## wherein R 3 V is chlorine or methyl and R 4 V is chlorine or methyl.
Claim 35
Dependent Claim 8 words
The compound of claim 33, which is N-phenyl-N-(N"-dimethylcarbamoyl)-N'-(3,4-dichlorophenyl)formamidine.
Claim 36
Dependent Claim 8 words
The compound of claim 33, which is N-phenyl-N-(N"-dimethylcarbamoyl)-N'-(3,4-dimethylphenyl)formamidine.
Claim 37
Dependent Claim 8 words
The compound of claim 33, which is N-phenyl-N-(N"-dimethylcarbamoyl)-N'-(4-chlorophenyl)formamidine.
Claim 38
Dependent Claim 8 words
The compound of claim 33, which is N-phenyl-N-(N"-dimethylcarbamoyl)-N'-(4-methylphenyl)formamidine.

References Cited (Backward Citations)

US3242209A Cited
US3340254A Cited
US3898277A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-29 1979-12-29 1980-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-29 1983-12-29 1984-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-29 1987-12-29 1988-06-29 $7700.00 Window Closed / Lapsed

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