← Back to Patent Explorer
USRE29508E Expired / Lapsed US ⏱️ 0.0 years remaining

Ring-substituted N-(2,2-difluoroalkanoyl)-o-phenylenediamine compounds

Assignee: Eli Lilly and Co
•
Filing: 1976-12-13
•
Granted: 1978-01-03
•
Expires: 1996-12-13
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Ring-substituted N-(2,2-difluoroalkanoyl)-o-phenylenediamine compounds useful as herbicides and as insecticides; and combinations of these compounds with known herbicides.

Inventors

  • 👤 George O. P. O'Doherty

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 15:26
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; A01N37/00; A01N37/18; A01N37/22; C; C07; C07C; C07C233/00

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 350 words
A compound selected from the group consisting of the compounds of the formulae: ##STR15## wherein R 0 represents a 2,2-difluoroalkanoyl radical of the formula ##STR16## wherein Y represents hydrogen, chlorine, fluorine, difluoromethyl, perfluoroalkyl of C 1 -C 6 , or radical of the formula ##STR17## wherein each Z independently represents hydrogen or halogen and n represents 0 or 1; R 1 represents hydrogen radical of the formula ##STR18## wherein Y represents loweralkyl of C 1 -C 4 or phenyl, benzoyl furoyl, naphthoyl, or substituted benzoyl of the formula ##STR19## wherein each Z' independently represents halo or nitro, Z" represents loweralkyl of C 1 -C 4 or loweralkoxy of C 1 -C 4 , p represents 0, 1, or 2, q represents 0 or 1, and the sum of p and q is 1-3; R 2 represents R 0 , R 1 , alkanoyl of C 1 -C 8 , loweralkenoyl of C 3 -C 4 , loweralkynoyl of C 3 -C 4 , halogenated loweralkanoyl of C 2 -C 4 bearing on any position or positions one or more halogen atoms, each independently selected, subject to the limitation that the alpha position bear at least one substituent moiety selected from the group consisting of hydrogen and halogen of atomic weight from 35 to 127, both inclusive; each R 3 independently represents halogen; R 4 represents nitro; R 5 represents trifluoromethyl, difluoromethyl, or difluorochloromethyl, and in compounds of Formula II, R 4 and R 5 are meta to one another; R 6 represents loweralkylsulfonyl of C 1 -C 4 and is located at the 4 or 5 position, and any R 4 group is meta to R 6 ; m represents 0-4; n represents 0-1; and in compounds of Formula I, the sum of m and n is an integer of from 1 to 4; subject to the further limitation that where R 1 or R 2 represents hydrogen, the ring position ortho to the --NH--R 1 or --NH--R 2 group bears one of the designated R 3 , R 4 , .Iadd.or .Iaddend.R 5 .[., or R 6 .]. moieties.
Claim 2
Dependent Claim 350 words
A compound selected from the group consisting of the compounds of the formulae: ##STR15## wherein R 0 represents a 2,2-difluoroalkanoyl radical of the formula ##STR16## wherein Y represents hydrogen, chlorine, fluorine, difluoromethyl, perfluoroalkyl of C 1 -C 6 , or radical of the formula ##STR17## wherein each Z independently represents hydrogen or halogen and n represents 0 or 1; R 1 represents hydrogen radical of the formula ##STR18## wherein Y represents loweralkyl of C 1 -C 4 or phenyl, benzoyl furoyl, naphthoyl, or substituted benzoyl of the formula ##STR19## wherein each Z' independently represents halo or nitro, Z" represents loweralkyl of C 1 -C 4 or loweralkoxy of C 1 -C 4 , p represents 0, 1, or 2, q represents 0 or 1, and the sum of p and q is 1-3; R 2 represents R 0 , R 1 , alkanoyl of C 1 -C 8 , loweralkenoyl of C 3 -C 4 , loweralkynoyl of C 3 -C 4 , halogenated loweralkanoyl of C 2 -C 4 bearing on any position or positions one or more halogen atoms, each independently selected, subject to the limitation that the alpha position bear at least one substituent moiety selected from the group consisting of hydrogen and halogen of atomic weight from 35 to 127, both inclusive; each R 3 independently represents halogen; R 4 represents nitro; R 5 represents trifluoromethyl, difluoromethyl, or difluorochloromethyl, and in compounds of Formula II, R 4 and R 5 are meta to one another; R 6 represents loweralkylsulfonyl of C 1 -C 4 and is located at the 4 or 5 position, and any R 4 group is meta to R 6 ; m represents 0-4; n represents 0-1; and in compounds of Formula I, the sum of m and n is an integer of from 1 to 4; subject to the further limitation that where R 1 or R 2 represents hydrogen, the ring position ortho to the --NH--R 1 or --NH--R 2 group bears one of the designated R 3 , R 4 , .Iadd.or .Iaddend.R 5 .[., or R 6 .]. moieties.
Claim 3
Dependent Claim 10 words
A compound of claim 1 which is of Formula I.
Claim 4
Dependent Claim 10 words
The compound of claim 2 which is N 1 -trifluoroacetyl-3'-nitro-5'-chloro-o-phenylenediamine.
Claim 5
Dependent Claim 10 words
The compound of claim 2 which is N 1 -trifluoroacetyl-3',4',5',6'-tetrachloro-o-phenylenediamine.
Claim 6
Dependent Claim 10 words
A compound of claim 1 which is of Formula II.
Claim 7
Dependent Claim 22 words
The compound of claim 5 which is N 1 -trifluoroacetyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine. .[.7. The compound of claim 5 which is N 1 -acetyl-N 2
Claim 8
Dependent Claim 3 words
-trifluoroacetyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine..]. 8. A
Claim 9
Dependent Claim 3 words
-trifluoroacetyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine..]. 8. A
Claim 10
Dependent Claim 21 words
compound of claim 1 which is of Formula III. 9. The compound of claim 8 which is N 1 ,N 2
Claim 11
Dependent Claim 12 words
-bis(trifluoroacetyl)-5'-(methylsulfonyl)-o-phenylenediamine. 10. The compound of claim 5 which is N 1 -(pentafluoropropionyl)-3'-nitro-5'-(trifluoromethyl).[.-0-.]..Iadd.-o-.Ia
Claim 12
Dependent Claim 12 words
ddend.phenylenediamine. 11. The compound of claim 5 which is N 1 -(2,2,3,3-tetrafluoropropionyl)-3'-nitro-5'-(trifluoromethyl)-o-phenylenediamine.

References Cited (Backward Citations)

US3407056A Cited
US3271435A Cited
US3478105A Cited
US3557211A Cited
US3869503A Cited
US3881018A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-01-02 1981-07-04 1982-01-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-01-02 1985-07-04 1986-01-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-01-02 1989-07-04 1990-01-03 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag