Patent US4236912A successfully refreshed from Google Patents.
US4236912A
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Quinolinyloxyphenoxy and quinolyinylthiophenoxy alkanoic acids and derivatives thereof and methods of herbicidal use
Assignee: Dow Chemical Co
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Filing: 1979-03-05
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Granted: 1980-12-02
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Expires: 1999-03-05
Abstract
Abstract Novel 2-quinolinyloxyphenoxy and 2-quinolinylthiophenoxy alkanoic acids, amides, salts, and esters thereof, and nitriles derived therefrom and 2-quinolinyloxy- and thio-phenoxy propanols and esters and ethers thereof having the following formula ##STR1## wherein: X and X' are independently F, Cl, Br, I, --CF 3 , CH 3 O--, --NO 2 , or --N(R') 2 , with the proviso that both cannot be --CF 3 , CH 3 O--, --NO 2 , or --NR' 2 , n is 0, 1, or 2 and n' is 0 or 1, Y is O or S, Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR', M is Na, K, Mg, Ca or --N(R") 4 , R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl, each R' is independently H or C 1 -C 4 alkyl and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl, are useful as herbicidal agents. Novel 2-quinolinyloxyphenols and 2-quinolinylthiophenols and simple metal salts thereof are useul in the preparation of the aforementioned active compounds.
Inventors
- 👤 Howard Johnston
- 👤 Lillian H. Troxell
- 👤 Jon S. Claus
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:15
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; A; A01; A01N; A01N43/00; A01N43/34; A01N43/40; A01N43/42; C07D215/18
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
142 words
A compound of the formula: ##STR7## wherein X and X' are independently F, Cl, Br, I, CF 3 --, CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be CF 3 --, CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 2
Dependent Claim
142 words
A compound of the formula: ##STR7## wherein X and X' are independently F, Cl, Br, I, CF 3 --, CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be CF 3 --, CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 3
Dependent Claim
38 words
The compound according to claim 1 wherein X is F, Cl, Br or I; n is 1 or 2, n' is 0; Y is O and Z is --CO 2 H, --CO 2 M or --CO 2 R.
Claim 4
Dependent Claim
10 words
The compound according to claim 2 wherein Z is --COOH.
Claim 5
Dependent Claim
10 words
The compound according to claim 3 wherein X is 6-chloro.
Claim 6
Dependent Claim
10 words
The compound according to claim 3 wherein X is 6-bromo.
Claim 7
Dependent Claim
10 words
The compound according to claim 3 wherein X is 6-fluoro.
Claim 8
Dependent Claim
20 words
The compound according to claim 1 wherein X is 6-chloro, X' is 3-chloro, Y is oxygen and Z is --COOH.
Claim 9
Dependent Claim
38 words
The compound according to claim 1 wherein X is F, Cl, Br, or I, n is 1 or 2, n' is 0, Y is sulfur and Z is --CO 2 H, --CO 2 M, or --CO 2 R.
Claim 10
Dependent Claim
16 words
The compound according to claim 8 wherein X is 6-bromo and Z is --CO 2 H.
Claim 11
Dependent Claim
16 words
The compound according to claim 8 wherein X is 6-chloro and Z is --CO 2 H.
Claim 12
Dependent Claim
171 words
A composition comprising an inert agricultural carrier and a herbicidally effective amount in the range of from about 0.003 percent by weight to about 95 percent by weight of a compound having the formula: ##STR8## wherein X and X' are independently F, Cl, Br, I, --CF 3 , CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be --CF 3 , CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 13
Dependent Claim
171 words
A composition comprising an inert agricultural carrier and a herbicidally effective amount in the range of from about 0.003 percent by weight to about 95 percent by weight of a compound having the formula: ##STR8## wherein X and X' are independently F, Cl, Br, I, --CF 3 , CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be --CF 3 , CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 14
Dependent Claim
38 words
The composition according to claim 11 wherein X is F, Cl, Br, or I; n is 1 or 2, n' is 0; Y is O; and Z is --CO 2 H, --CO 2 M or --CO 2 R.
Claim 15
Dependent Claim
12 words
The composition according to claim 12 wherein Z is --CO 2 H.
Claim 16
Dependent Claim
10 words
The composition according to claim 13 wherein X is 6-chloro.
Claim 17
Dependent Claim
10 words
The composition according to claim 13 wherein X is 6-bromo.
Claim 18
Dependent Claim
10 words
The composition according to claim 13 wherein X is 6-fluoro.
Claim 19
Dependent Claim
20 words
The composition according to claim 11 wherein X is 6-chloro, X' is 3-chloro, Y is oxygen and Z is --COOH.
Claim 20
Dependent Claim
38 words
The composition according to claim 11 wherein X is F, Cl, Br, or I, n is 1 or 2, n' is 0, Y is sulfur and Z is --CO 2 H, --CO 2 M, or --CO 2 R.
Claim 21
Dependent Claim
16 words
The composition according to claim 18 wherein X is 6-bromo and Z is --CO 2 H.
Claim 22
Dependent Claim
16 words
The composition according to claim 18 wherein X is 6-chloro and Z is --CO 2 H.
Claim 23
Independent Claim
172 words
The method of controlling undesired plant growth which comprises applying to the locus of said plants a herbicidally effective amount in the range of from 0.01 to 20 lbs/acre of a compound having the formula: ##STR9## wherein X and X' are independently F, Cl, Br, I, --CF 3 , CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be --CF 3 , CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 24
Independent Claim
172 words
The method of controlling undesired plant growth which comprises applying to the locus of said plants a herbicidally effective amount in the range of from 0.01 to 20 lbs/acre of a compound having the formula: ##STR9## wherein X and X' are independently F, Cl, Br, I, --CF 3 , CH 3 O--, --NO 2 , or --N(R') 2 ; with the proviso that both cannot be --CF 3 , CH 3 O--, --NO 2 , or --NR' 2 ; n is 0, 1 or 2; n' is 0 or 1; Y is O or S; Z is --CO 2 H, --CO 2 M, --CO 2 R, --COSR, --CONR' 2 , --CSNH 2 , --CN, --CH 2 OR' or --CH 2 O 2 CR'; M is Na, K, Mg, Ca or --N(R") 4 ; R" is H, C 1 -C 4 alkyl or C 2 -C 3 hydroxyalkyl; each R' is independently H or C 1 -C 4 alkyl; and R is C 1 -C 8 alkyl or C 3 -C 6 alkoxyalkyl.
Claim 25
Dependent Claim
38 words
The method according to claim 21 wherein X is F, Cl, Br or I; n is 1 or 2; n' is 0; Y is O and Z is --CO 2 H, --CO 2 M, or --CO 2 R.
Claim 26
Dependent Claim
12 words
The method according to claim 22 wherein X is --CO 2 H.
Claim 27
Dependent Claim
10 words
The method according to claim 23 wherein X is 6-chloro.
Claim 28
Dependent Claim
10 words
The method according to claim 23 wherein X is 6-bromo.
Claim 29
Dependent Claim
10 words
The method according to claim 23 wherein X is 6-fluoro.
Claim 30
Dependent Claim
22 words
The method according to claim 21 wherein X is 6-chloro, X' is 3-chloro, Y is oxygen and Z is --CO 2 H.
Claim 31
Dependent Claim
31 words
The method according to claim 21 wherein X is F, Cl, Br or I; n is 1 or 2; n' is 0; Y is sulfur and Z is --CO 2 H.
Claim 32
Dependent Claim
16 words
The method according to claim 28 wherein X is 6-bromo and Z is --CO 2 H.
Claim 33
Dependent Claim
16 words
The method according to claim 28 wherein X is 6-chloro and Z is --CO 2 H.
Claim 34
Dependent Claim
25 words
The method according to claim 21 wherein the compound is applied in preemergent operations in an amount of from 0.05 to 4 pounds per acre.
Claim 35
Dependent Claim
12 words
The method of claim 31 wherein the compound employed is 2-(4-((6-chloro-2-quinolinyl)oxy)phenoxy)propionic acid.
Claim 36
Dependent Claim
25 words
The method according to claim 21 wherein the compound is applied in postemergent operations in an amount of from 0.5 to 5 pounds per acre.
Claim 37
Dependent Claim
12 words
The method of claim 33 wherein the compound employed is 2-(4-((6-fluoro-2-quinolinyl)oxy)phenoxy)propionic acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-12-02 | 1984-06-02 | 1984-12-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-02 | 1988-06-02 | 1988-12-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-02 | 1992-06-02 | 1992-12-02 | $7700.00 | Window Closed / Lapsed |