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US3937729A Expired / Lapsed US ⏱️ 0.0 years remaining

Meta-bis anilide derivatives and their utility as herbicides

Assignee: Zeneca Inc
•
Filing: 1973-03-19
•
Granted: 1976-02-10
•
Expires: 1993-03-19
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Abstract

Abstract Compounds corresponding to the formula: ##SPC1## In which R 1 and R 2 are, independently, hydrogen, alkyl, alkoxyalkyl, cycloalkyl, pinonyl, ethylcycloalkyl, lower alkenyl, halogenated lower alkyl, benzyl, ethylphenyl, 2,4-dichlorophenoxy-methylene, styryl, furyl, phenyl or substituted phenyl in which the substituents are nitro, halogen, methyl, or methoxy; R 3 and R 4 are, independently, hydrogen or lower alkyl; X and Y are independently oxygen or sulfur; and Z is halogen, nitro, amino, lower alkyl, lower alkoxy or trifluoromethyl and n is an integer having a value from 0 to 4. The above compounds are effective herbicides, particularly for the control of grasses and broadleaf plants with both pre-emergence and post-emergence activity. Representative compounds are: m-propionamidobutyranilide, m-bis-2,2-dimethylvaleranilide, m-isobutyramido trichloroacetanilide, m-isobutyramido-2-ethylbutyranilide, m-t-butylacetamidopropionanilide, and 3'-N-ethyl propionamido-propionalide. This application is a continuation of application Ser. No. 180,916, filed Sept. 15, 1971, which is a continuation of application Ser. No. 20,104, filed Mar. 16, 1970, which is a continuation-in-part of application Ser. No. 741,267, filed July 1, 1968, which is a continuation-in-part of application Ser. No. 659,865, filed Aug. 11, 1967, all now abandoned.

Inventors

  • 👤 Eugene G. Teach

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 16:39
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68

Claims Analysis

Total Claims: 50
Claim 1
Independent Claim 19 words
A compound having the formula ##SPC4## in which R 2 is halogenated lower alkyl, and R 1 is alkyl.
Claim 2
Dependent Claim 19 words
A compound having the formula ##SPC4## in which R 2 is halogenated lower alkyl, and R 1 is alkyl.
Claim 3
Dependent Claim 17 words
A compound according to claim 1 in which R 1 is ethyl and R 2 is 1-bromo-1-methylethyl.
Claim 4
Dependent Claim 17 words
A compound according to claim 1 in which R 1 is isopropyl and R 2 is trichloromethyl.
Claim 5
Dependent Claim 17 words
A compound according to claim 1 in which R 1 is isopropyl and R 2 is 1-chloroethyl.
Claim 6
Dependent Claim 17 words
A compound according to claim 1 in which R 1 is isopropyl and R 2 is 1-bromo-1-methylethyl.
Claim 7
Dependent Claim 17 words
A compound according to claim 1 in which R 1 is ethyl and R 2 is trifluoromethyl.
Claim 8
Dependent Claim 17 words
A compound according to claim 1 in which R 2 is 1-bromo-iso-propyl and R 1 is ethyl.
Claim 9
Dependent Claim 17 words
A compound according to claim 1 in which R 2 is 1,1-dichloroethyl and R 1 is ethyl.
Claim 10
Dependent Claim 17 words
A compound according to claim 1 in which R 2 is trifluoromethyl and R 1 is 1,1-dimethylbutyl.
Claim 11
Dependent Claim 17 words
A compound according to claim 1 in which R 2 is 1,1-dimethyl-2-chloroethyl and R 1 is ethyl.
Claim 12
Dependent Claim 17 words
A compound according to claim 1 in which R 2 is 1,1-dimethyl-2-chloroethyl and R 1 is 1,1-dimethylbutyl.
Claim 13
Dependent Claim 6 words
The compound having the formula ##SPC5##
Claim 14
Dependent Claim 6 words
The compound having the formula ##SPC5##
Claim 15
Dependent Claim 17 words
A compound having the formula ##SPC6## in which R 1 is lower alkenyl, R 2 is alkyl.
Claim 16
Dependent Claim 17 words
A compound having the formula ##SPC6## in which R 1 is lower alkenyl, R 2 is alkyl.
Claim 17
Dependent Claim 16 words
A compound according to claim 13 in which R 1 is 2,2-dimethylvinyl, R 2 is tert-butyl.
Claim 18
Dependent Claim 16 words
A compound according to claim 13 in which R 1 is 2,2-dimethylvinyl, R 2 is 1,1-dimethylbutyl.
Claim 19
Dependent Claim 16 words
A compound according to claim 13 in which R 1 is 2,2-dimethylvinyl, R 2 is ethyl.
Claim 20
Dependent Claim 16 words
A compound according to claim 13 in which R 1 is vinyl, R 2 is ethyl.
Claim 21
Dependent Claim 17 words
A compound having the formula ##SPC7## in which R 1 is benzyl and R 2 is alkyl.
Claim 22
Dependent Claim 17 words
A compound having the formula ##SPC7## in which R 1 is benzyl and R 2 is alkyl.
Claim 23
Dependent Claim 12 words
A compound according to claim 18 in which R 2 is tert-butyl.
Claim 24
Dependent Claim 12 words
A compound according to claim 18 in which R 2 is sec-butyl.
Claim 25
Dependent Claim 12 words
A compound according to claim 18 in which R 2 is 1-methylbutyl.
Claim 26
Dependent Claim 12 words
A compound according to claim 18 in which R 2 is 1,1-dimethylbutyl.
Claim 27
Dependent Claim 17 words
A compound having the formula ##SPC8## in which R 1 is chlorophenyl and R 2 is alkyl.
Claim 28
Dependent Claim 17 words
A compound having the formula ##SPC8## in which R 1 is chlorophenyl and R 2 is alkyl.
Claim 29
Dependent Claim 17 words
A compound according to claim 23 in which R 1 is 2-chlorophenyl and R 2 is ethyl.
Claim 30
Dependent Claim 17 words
A compound according to claim 23 in which R 1 is 4-chlorophenyl and R 2 is ethyl.
Claim 31
Dependent Claim 17 words
A compound according to claim 23 in which R 1 is 4-chlorophenyl and R 2 is tert-butyl.
Claim 32
Dependent Claim 17 words
A compound having the formula ##SPC9## in which R 1 is styryl and R 2 is alkyl.
Claim 33
Dependent Claim 17 words
A compound having the formula ##SPC9## in which R 1 is styryl and R 2 is alkyl.
Claim 34
Dependent Claim 12 words
A compound according to claim 27 in which R 2 is ethyl.
Claim 35
Dependent Claim 17 words
A compound having the formula ##SPC10## in which R 1 is 2,4,4-trimethylpentyl and R 2 is 1,1-dimethylbutyl.
Claim 36
Dependent Claim 17 words
A compound having the formula ##SPC10## in which R 1 is 2,4,4-trimethylpentyl and R 2 is 1,1-dimethylbutyl.
Claim 37
Dependent Claim 16 words
A compound having the formula ##SPC11## in which R 1 is 1,1-dimethylbutyl, R 2 is neopentyl.
Claim 38
Dependent Claim 16 words
A compound having the formula ##SPC11## in which R 1 is 1,1-dimethylbutyl, R 2 is neopentyl.
Claim 39
Dependent Claim 17 words
A compound having the formula ##SPC12## in which R 1 is tert.-butyl and R 2 is neopentyl.
Claim 40
Dependent Claim 17 words
A compound having the formula ##SPC12## in which R 1 is tert.-butyl and R 2 is neopentyl.
Claim 41
Dependent Claim 17 words
A compound having the formula ##SPC13## in which R 1 is 1-methylbutyl, and R 2 is tert.-butyl.
Claim 42
Dependent Claim 17 words
A compound having the formula ##SPC13## in which R 1 is 1-methylbutyl, and R 2 is tert.-butyl.
Claim 43
Dependent Claim 17 words
A compound having the formula ##SPC14## in which R 1 is 3,4-dichlorophenyl and R 2 is ethyl.
Claim 44
Dependent Claim 17 words
A compound having the formula ##SPC14## in which R 1 is 3,4-dichlorophenyl and R 2 is ethyl.
Claim 45
Dependent Claim 17 words
A compound having the formula ##SPC15## in which R 1 is 2,4-dichlorophenyl and R 2 is tert.-butyl.
Claim 46
Dependent Claim 17 words
A compound having the formula ##SPC15## in which R 1 is 2,4-dichlorophenyl and R 2 is tert.-butyl.
Claim 47
Dependent Claim 17 words
A compound having the formula ##SPC16## in which R 1 is cyclopropyl and R 2 is tert.-butyl.
Claim 48
Dependent Claim 17 words
A compound having the formula ##SPC16## in which R 1 is cyclopropyl and R 2 is tert.-butyl.
Claim 49
Dependent Claim 175 words
Compound having the formula ##SPC17## in which R 1 and R 2 are as follows: a. R 1 is 2,2-dimethylpropyl and R 2 is isopropyl b. R 1 is isopropyl and R 2 is 1-ethylpropyl c. R 1 is isopropyl and R 2 is 1,1-dimethylbutyl d. R 1 is isopropyl and R 2 is 1-methylbutyl e. R 1 is 2-methylbutyl and R 2 is tert.-butyl f. R 1 is 1,1-dimethylbutyl and R 2 is tert.-butyl g. R 1 is tert.-butyl and R 2 is 2,2-dimethylpropyl h. R 1 is 3-methylbutyl and R 2 is tert.-butyl i. R 1 is 1-methylpropyl and R 2 is tert.-butyl j. R 1 is 2,2-dimethylpropyl and R 2 is 1-methylpropyl k. R 1 is 2,2-dimethylpropyl and R 2 is 1-methylbutyl l. R 1 is 1-methylbutyl and R 2 is 1,1-dimethylbutyl m. R 1 is 1-methylpropyl and R 2 is 1-methylbutyl n. R 1 is 2-methylbutyl and R 2 is 1-methylbutyl o. R 1 is 2,2-dimethylbutyl and R 2 is 1-methylbutyl p. R 1 is 2-methylbutyl and R 2 is 1,1-dimethylbutyl.
Claim 50
Dependent Claim 175 words
Compound having the formula ##SPC17## in which R 1 and R 2 are as follows: a. R 1 is 2,2-dimethylpropyl and R 2 is isopropyl b. R 1 is isopropyl and R 2 is 1-ethylpropyl c. R 1 is isopropyl and R 2 is 1,1-dimethylbutyl d. R 1 is isopropyl and R 2 is 1-methylbutyl e. R 1 is 2-methylbutyl and R 2 is tert.-butyl f. R 1 is 1,1-dimethylbutyl and R 2 is tert.-butyl g. R 1 is tert.-butyl and R 2 is 2,2-dimethylpropyl h. R 1 is 3-methylbutyl and R 2 is tert.-butyl i. R 1 is 1-methylpropyl and R 2 is tert.-butyl j. R 1 is 2,2-dimethylpropyl and R 2 is 1-methylpropyl k. R 1 is 2,2-dimethylpropyl and R 2 is 1-methylbutyl l. R 1 is 1-methylbutyl and R 2 is 1,1-dimethylbutyl m. R 1 is 1-methylpropyl and R 2 is 1-methylbutyl n. R 1 is 2-methylbutyl and R 2 is 1-methylbutyl o. R 1 is 2,2-dimethylbutyl and R 2 is 1-methylbutyl p. R 1 is 2-methylbutyl and R 2 is 1,1-dimethylbutyl.

References Cited (Backward Citations)

US2231611A Cited
US2317130A Cited
US2402792A Cited
US2647815A Cited
DE936395C Cited
US3188346A Cited
US3424767A Cited
FR1368619A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-02-09 1979-08-11 1980-02-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-02-09 1983-08-11 1984-02-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-02-09 1987-08-11 1988-02-10 $7700.00 Window Closed / Lapsed

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