Cycloimido-substituted benzofused heterocyclic herbicides

Details Cycloimido-substituted benzofused heterocyclic herbicides Cycloimido-substituted benzofused heterocyclic herbicides

2000-04-12

2002-03-05

Kifle, Bruck (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S276000, C504S285000, C504S286000, C548S221000, C548S222000, C548S224000, C548S305100, C548S473000, C548S476000, C548S477000, C548S478000, C548S479000

Reexamination Certificate

active

06352958

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates generally to novel herbicidal compounds and methods for their use in controlling unwanted plant species in agriculture. In particular, the present invention pertains to cycloimido-substituted benzofused heterocyclic herbicides, and more particularly it pertains to herbicides in which the benzofused heterocycle is a benzofuran, benzimidazole, a 2,3-dihydrobenzimidazole, or indole having a cycloimido moiety which is a 1 -substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring.
SUMMARY OF THE INVENTION
It has now been found that certain cycloimido-substituted benzofused heterocyclic compounds are useful as pre-emergent and postemergent herbicides. These novel compounds are represented by formula I:
where J is a 1-substituted-6-trifluoromethyl-2,4-pyrimidinedione-3-yl, a 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dion-1-yl, a 3,4,5,6-tetrahydrophthalimid-1-yl, a 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, a 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl, or a 1,6,8-triazabicyclo[4.3.0]-nonane-7,9-dion-8-yl ring attached at the 7 position of a benzofuran, benzoxazole, 2,3-dihydrobenzimidazole, indole or benzimidazole, and X is selected from hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, and amino. Preferred R groups are optionally substituted alkyl groups.
DETAILED DESCRIPTION OF THE INVENTION
Certain cycloimido-substituted benzofused heterocyclic compounds have now been found to be useful as pre- and postemergent herbicides. These compounds are represented by formula I:
where
(1) A is nitrogen double-bonded to position 2 and B is oxygen;
(2) A is oxygen and B is CR′ double bonded to position 2;
(3) A is NH and B is nitrogen double-bonded to position 2;
(4) A is nitrogen double bonded to position 2 and B is NR
2
;
(5) A is CH double bonded to position 2 and B is NR
2
;
(6) A is NH and B is CR′ double bonded to position 2; or
(7) A and B are NH
R is hydrogen, hydroxy, mercapto, straight or branched chain lower alkyl, cycloalkyl, alkoxy, aryl, heteroaryl, alkenyl, haloalkyl, hydroxyalkyl, haloaryl, alkoxyaryl, arylalkyl, aryloxyalkyl, haloarylalkyl, alkylthio, heterocyclyl, alkoxyalkyl, alkoxylalkyloxyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, aminocarbonyloxyalkyl, aminoalkyl, cyanoalkyl, aminoalkenyl, carboxy, carboxyalkyl, alkylcarboxy, alkylcarboxyalkyl, formyl, aminocarbonyl, amino, oxygen, cyano, nitro, alkylsulfonyl, aminosulfonyl, alkylsulfonylamino, alkoxycarbonyloxyalkyl, alkylcarboxylalkoxy, alkoxycarbonylamino, alkoxycarbonylalkylaminoalkyl, aryliminoalkyl, (aryl)(alkoxy)alkyl, (aryl)(alkylcarbonyloxy)alkyl, arylalkoxyalkyl, cyanoalkylthio, alkynylalkylthio, arylalkylthio, cyanothio, cyanothioalkyl, alkoxycarbonylalkylthio, aminocarbonylalkylthio, alkenylalkylthio, haloalkylalkynylalkylthio, aminocarbonyloxyalkyl, arylalkylcarbonylaminoalkyl, (hydroxy)(aryl)alkyl, alkylcarbonylaminoalkyl, alkylsulfonylaminoalkyl, aminocarbonylalkyl, alkoxycarbonyl, and alkenyloxy, where the amino group may be substituted with one or two substituents independently selected from alkyl, hydroxy, alkoxy, carboxy, aryl, alkylsufonyl, or haloalkylsulfonyl;
R
1
is hydrogen, lower alkyl, or haloalkyl;
R
2
is hydrogen, alkyl, haloalkyl, CO
2
(alkyl), CH
2
CO
2
(alkyl), CH
2
CONH-alkyl, CH
2
CON(alkyl)
2
, CH
2
CO
2
H, CH
2
OCH
3
, SO
2
(alkyl), CH
2
CH═CH
2
, CH
2
C≡CH.
X is selected from hydrogen, F, Cl, Br, alkyl, haloalkyl, CN, NO
2
, and NH
2
;
n is 0-3;
J is selected from
and
R
3
is selected from hydrogen, alkyl, haloalkyl, CH
2
CN, CH
2
CH═CH
2
, CH
2
C≡CH, CH
2
CO
2
(alkyl), CH
2
OCH
3
, and NH
2
.
Preferred compounds are those of formula I where R is CH
3
, CH
2
CH
3
, C(CH
3
)
2
OH, CH
2
CH
2
OH, CH(CH
3
)
2
, t-butyl, CF
3
, CH(F)CH
3
, CF
2
CF
3
, C(CH
3
)
2
OCOCH
3
, C(CH
3
)
2
NHSO
2
CH
3
, CH
2
CH
2
CH
2
C≡N CH
2
CH
2
CO
2
CH
3
, and CON(CH
3
)
2
; X is a chlorine, bromine or fluorine substituted in one or both of positions 4 and 6; J is
and R
3
is CH
3
or NH
2
.
One aspect of the present invention relates to compounds of formula I in which A is nitrogen double-bonded to position 2 and B is oxygen, and R, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A is oxygen and B is CR
1
double bonded to position 2, and R, R
1
, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A is NH and B is nitrogen double-bonded to position 2, and R, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A is nitrogen double bonded to position 2 and B is NR
2
,and R, R
2
, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A is CH double bonded to position 2 and B is NR
2
, and R, R
2
, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A is NH and B is CR
1
double bonded to position 2, and R, R
1
, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I in which A and B are NH and R, R
1
, R
3
, J, X and n are as described above.
Another aspect of the present invention relates to compounds of formula I where J is not
when: A is oxygen and B is CR
1
double bonded to position 2; A is CH double bonded to position 2 and B is NR
2
; or A is NH and B is CR
1
double bonded to position 2; and R, R
1
, R
3
, X, and n are as described above.
As shown in the specification a wide range of substituents is described for position B in compounds of formula I whereas position A is generally unsubstituted. It was found that some herbicidal activity is retained when a methyl substituent is placed at position A, but that substitution at that position generally causes a sharp decrease in activity.
Certain intermediates of the present invention are novel. These include compounds of formula II:
where Y is NO
2
, NH
2
, or —NHN═C(CH
3
)R; Z is hydrogen, F, NH
2
, or OH; and R, J, X, and n are as described above; with the proviso that when Y is —NHN═C(CH
3
)R, Z is hydrogen.
As used in this specification and unless otherwise indicated, the terms “alkyl,” “alkenyl,” “alkynyl,” “h aloalkyl,” and “alkoxy” used alone or as part of a larger moiety, includes straight or branched carbon chains of 1 to 6 carbon atoms. “Halogen” refers to fluorine, bromine or chlorine. “THF” means tetrahydrofuran, “DMF” means N,N-dimethylformamide, and “DBU” means 1,8-diazabicyclo[5.4.0]undec-7-ene. When “n” in “X
(n)
” is 2 or 3, the substituents X may be the same or different from one another.
a) 70% HNO
3
/ H
2
SO
4
, 0-5° C.; (b) NaOSi(CH
3
)
3
, MeOH, dioxane; (c) Fe, EtOH, acetic acid, HCl, heat; (d) CF
3
C(NH
2
)═CO
2
CH
2
CH
5
, NaOSi(CH
3
)
3
, DBU, DMF; (e) CH
3
I, K
2
CO
3
, DMF, 60-80° C.; (f) HCl, NaNO
2
, NaI, H
2
O; (g) BBr
3
, CH
2
Cl
2
; (h) HC≡CR, Pd(Ph
3
P)
2
Cl
2
, Cul, triethylamine.
Benzofurans of formula I, where A is oxygen and B is CH double bonded to position 2, may be generally prepared as shown in Scheme 1. Starting with an appropriately substituted fluoroaniline derivative 1, nitration provides intermediate 2. Displacement of the fluorine of 2 with a methoxy group as shown in step b, followed by reduction of the nitro group as shown in step c provide the methoxyaniline 3. The methoxyaniline 3 is a versatile intermediate from which a number of compounds of the present invention can be made by attachment of various J groups. For example, a uracil ring may

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