Substituted phenylheterocyclic herbicides

Details Substituted phenylheterocyclic herbicides Substituted phenylheterocyclic herbicides

1999-04-15

2002-03-19

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S221000, C504S255000, C504S267000, C504S275000, C504S281000, C504S270000, C544S058200, C544S139000, C544S145000, C544S148000, C544S176000, C544S105000, C548S152000, C548S159000, C548S178000, C548S221000, C548S302700, C548S303700, C548S304400, C548S311100, C548S311400, C548S311700, C548S360100, C548S360500

Reexamination Certificate

active

06358885

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain substituted fused heterocyclic compounds which are useful as herbicides and their agriculturally suitable compositions as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 5,032,165 discloses herbicidal compounds of the formula
SUMMARY OF THE INVENTION
The invention comprises novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergent and/or postemergent herbicides and/or plant growth regulants
wherein
Q is
G
1
is CR
1
or N;
G
2
is CR
4
or N;
A is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, OR
10
, SR
10
or halogen;
B is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
4
alkenyl or C
3
-C
4
alkynyl;
A and B can be taken together as X—Y—Z to form a fused ring such that X is connected to nitrogen and Z is connected to carbon;
X is CHR
2
, CH
2
CH
2
or CR
2
═CR
3
;
Y is CHR
5
, CR
5
═CR
6
, CHR
5
CHR
6
, NR
7
, O or S(O)
n
;
Z is CHR
8
, CH
2
CH
2
, CR
8
═CR
9
, NR
7
, O or S(O)
n
;
n is O, 1 or 2;
R
1
and R
4
are independently halogen or CN;
R
2
, R
3
, R
5
, R
6
, R
8
and R
9
are independently H, halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
7
is H, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
W is O or S;
R
10
is C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
11
is halogen;
R
12
is H, C
1
-C
8
alkyl, C
1
-C
8
,haloalkyl, halogen, OH, OR
17
, SH, S(O)
n
R
17
, COR
17
, CO
2
R
17
, C(O)SR
17
, C(O)NR
19
R
20
, CHO, CR
19
═NOR
26
, CH═CR
27
CO
2
R
17
, CH
2
CHR
27
CO
2
R
17
, CO
2
N═CR
21
R
22
, NO
2
, CN, NHSO
2
R
23
, NHSO
2
NHR
23
, NR
17
R
28
, NH
2
or phenyl optionally substituted with R
29
;
R
13
is C
1
-C
2
alkyl, C
1
-C
2
haloalkyl, OCH
3
, SCH
3
, OCHF
2
, halogen, CN or NO
2
;
R
14
is H, C
1
-C
3
alkyl or halogen;
R
15
is H, C
1
-C
3
alkyl, halogen, C
1
-C
3
haloalkyl, cyclopropyl, vinyl, C
2
alkynyl, CN, C(O)R
28
, CO
2
R
28
, C(O)NR
28
R
30
, CR
24
R
25
CN, CR
24
R
25
C(O)R
28
, CR
24
R
25
CO
2
R
28
, CR
24
R
25
C(O)NR
28
R
30
, CHR
24
OH, CHR
24
OC(O)R
28
or OCHR
24
OC(O)NR
28
R
30
;
when Q is Q-2 or Q-6, R
14
and R
15
together with the carbon to which they are attached can be C═O;
R
16
is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkoxyalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or
R
17
is C
1
-C
8
alkyl; C
3
-C
8
cycloalkyl; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
1
-C
8
haloalkyl; C
2
-C
8
alkoxyalkyl; C
2
-C
8
alkylthioalkyl; C
2
-C
8
alkylsulfinylalkyl; C
2
-C
8
alkylsulfonylalkyl, C
4
-C
8
alkoxyalkoxyalkyl; C
4
-C
8
cycloalkylalkyl; C
4
-C
8
alkenoxyalkyl; C
4
-C
8
alkynoxyalkyl; C
6
-C
8
cycloalkoxyalkyl; C
4
-C
8
alkenyloxyalkyl; C
4
-C
8
alkynyloxyalkyl; C
3
-C
8
haloalkoxyalkyl; C
4
-C
8
haloalkenoxyalkyl; C
4
-C
8
haloalkynoxyalkyl; C
6
-C
8
cycloalkylthioalkyl; C
4
-C
8
alkenylthioalkyl; C
4
-C
8
alkynylthioalkyl; C
1
-C
4
alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl; C
4
-C
8
trialkylsilylalkyl; C
3
-C
8
cyanoalkyl; C
3
-C
8
halocycloalkyl; C
3
-C
8
haloalkenyl; C
5
-C
8
alkoxyalkenyl; C
5
-C
8
haloalkoxyalkenyl; C
5
-C
8
alkylthioalkenyl; C
3
-C
8
haloalkynyl; C
5
-C
8
alkoxyalkynyl; C
5
-C
8
haloalkoxyalkynyl; C
5
-C
8
alkylthioalkynyl; C
2
-C
8
alkyl carbonyl; benzyl optionally substituted with halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl; CHR
24
COR
18
; CHR
24
P(O) (OR
18
)
2
; CHR
24
P(S) (OR
18
)
2
; CHR
24
C(O)NR
19
R
20
; CHR
24
C(O)NH
2
; CHR
24
CO
2
R
18
;
CO
2
R
18
; SO
2
R
18
; phenyl optionally substituted with R
29
;
R
18
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl;
R
19
and R
21
are independently H or C
1
-C
4
alkyl;
R
20
and R
22
are independently C
1
-C
4
alkyl or phenyl optionally substituted with halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl;
R
19
and R
20
may be taken together as —(CH
2
)
5
—, —(CH
2
)
4
— or —CH
2
CH
2
OCH
2
CH
2
—, each ring optionally substituted with C
1
-C
3
alkyl, phenyl or benzyl;
R
21
and R
22
may be taken together with the carbon to which they are attached to form C
3
-C
8
cycloalkyl;
R
23
is C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
24
and R
25
are independently H or C
1
-C
4
alkyl;
R
26
is H, C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl;
R
27
is H, C
1
-C
4
alkyl or halogen;
R
28
and R
30
are independently H or C
1
-C
4
alkyl; and
R
29
is C
1
-C
2
alkyl, C
1
-C
2
haloalkyl, OCH
3
, SCH
3
, OCHF
2
, halogen, CN or NO
2
;
and their corresponding N-oxides and agriculturally suitable salts provided that
1) the sum of X, Y, and Z is no greater than 5 atoms in length and only one of Y and Z can be other than a carbon containing link;
2) when A and B are other than taken together as X—Y—Z then G
1
is N and G
2
is CR
4
;
3) when R
12
is CO
2
R
17
, C(O)SR
17
, CH═CR
27
CO
2
R
17
or CH
2
CHR
27
CO
2
R
17
then R
17
is other than C
1
haloalkyl and when R
17
is CHR
24
CO
2
R
18
or CO
2
R
18
then R
18
is other than C
1
haloalkyl; and
4) when G
1
is N then G
2
is CR
4
, and when G
2
is N then G
1
is CR
1
.
In the above definitions, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl”, includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy, the different butoxy isomers, etc. Alkenyl and alkynyl include straight chain or branched alkenes and alkynes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “halogen”, either alone or in compound words such as “haloalkyl”, means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH
2
CH
2
F, CF
2
CF
3
and CH
2
CHFCl.
The compounds of the invention preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:
1) Compounds of Formula I wherein R
2
, R
3
, R
5
, R
6
, R
8
and R
9
are independently H, F, CH
3
or CF
3
.
2) Compounds of Preferred 1 wherein
R
12
is H, OR
17
, SR
17
or CO
2
R
17
;
R
13
is halogen or CN.
3) Compounds of Preferred 2 wherein
Q is Q-1, Q-2, Q-4 or Q-5;
A and B are taken together as X—Y—Z;
X is CHR
2
;
Y is CHR
5
or CHR
5
CHR
6
;
Z is CHR
8
;
R
2
, R
3
, R
5
, R
6
, R
8
and R
9
are independently H or F;
R
17
is C
1
-C
4
alkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
2
-C
4
alkoxyalkyl, C
1
-C
4
haloalkyl,
C
3
-C
4
haloalkenyl or C
3
-C
4
haloalkynyl.
4) Compounds of Formula I wherein G
1
is N.
5) Compounds of Formula I wherein G
2
is N.
The compounds of the invention specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are the compounds of Preferred 3 which are:
3-bromo-2-[4-chloro-2-fluoro-5-(2-propynyloxy)-phenyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine;
3-chloro-2-[4-chloro-2-

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