Substituted triazoles imidazoles and pyrazoles as herbicides

Details Substituted triazoles imidazoles and pyrazoles as herbicides Substituted triazoles imidazoles and pyrazoles as herbicides

2000-06-13

2001-07-10

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S229000, C504S235000, C504S237000, C504S238000, C504S243000, C544S182000, C544S220000, C544S239000, C544S241000, C544S310000, C548S131000, C548S132000, C548S133000, C548S138000, C548S143000, C548S144000, C548S262400, C548S263400, C548S263800

Reexamination Certificate

active

06258751

ABSTRACT:

The present invention relates to novel heterocyclic compounds and their agronomically suitable salts, methods for the use of these compounds in controlling unwanted plant species, and the use of herbicidal compositions containing these compounds.
The presence of unwanted plant species causes substantial damage to useful crops, especially agricultural products that satisfy the human being's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean. The current population explosion and concomitant world food and fiber shortage demand improvements in efficiency of producing these crops. Prevention or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of unwanted plant species is one way of improving this efficiency. Though many herbicides are available, the need still exists for more effective herbicides.
The compounds of the present invention in general show a usefully improved level of crop safety on soybean, corn or wheat than the known compounds.
EP 0 083 055 A2, published Jul. 6, 1983, discloses herbicidal compounds of the following formula (i)
wherein
R
1
is hydrogen, alkyl, lower cycloalkyl, lower alkyl(lower)cycloalkyl, lowercycloalkyl(lower)alkyl, lower alkoxyl(lower)alkyl, lower alkenyl, lower cycloalkenyl, lower cycloalkenyl(lower)alkyl, phenyl, cyano(lower)alkyl, lower alkynyl, lower alkylideneamino, lower alkylthio(lower)alkyl, benzyl, halo(lower)alkyl or lower cycloalkylideneamino;
R
2
is hydrogen, lower alkyl, lower alkoxyl;
X is chlorine or bromine;
Y is oxygen or imino; and
Z is oxygen or sulfur.
EP 0 273 417 A1 published Jul. 6, 1988 discloses the herbicidal compounds having the formula (ii)
wherein
each of X and Y is hydrogen or halogen;
Z is —SCH(R)COOR
1
;
R is hydrogen, alkyl, and R
1
is alkyl, cycloalkyl, or alkoxyalkyl, or COOQ wherein Q is alkyl, or Y and Z together form
bonded to phenyl ring, wherein R
2
is H or alkyl, and R
3
is alkyl, alkenyl, or alkynyl.
The present invention relates to novel herbicidal compounds and methods for their use in controlling unwanted plant species and their use in herbicidal compositions in agriculture. In particular, the present invention pertains to substituted and unsubstituted triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group.
It has now been found that certain triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group are useful as pre-emergent and post-emergent herbicides. These novel compounds are represented by formula I
wherein
R
1
is selected from H, F, Br, Cl, NO
2
and CN;
R
2
is selected from F, Cl, Br, H and CN;
R
3
is selected from H and CN; and alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, cycloalkenyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted;
R
4
and R
5
are each independently selected from H, halo and CN; and alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, CO
2
R
6
, CONR
6
R
13
, OR
6
, SR
6
, SO
2
R
6
, NR
6
R
13
, SO
2
NR
6
R
13
, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted;
R
6
is selected from H, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted;
R
7
is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl and COR
9
, all of which may be further substituted;
R
8
is selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted;
R
9
is selected from H, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, alkenyl, alkynyl, haloalkyl and cycloalkyl, all of which may be further substituted;
R
10
is selected from H, halo, NH
2
, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, haloalkyl, CN, CO
2
(alkyl), CONH(alkyl), CON(alkyl)
2
wherein each alkyl may be the same or different, CH
2
CN, CH
2
CH═CH
2
, CH
2
C≡CH, CH
2
CO
2
(alkyl), CH
2
OCH
3
and CH
2
-1,2,4-triazole, all of which may be further substituted;
R
11
is selected from H, CN, alkyl, haloalkyl and CO
2
(alkyl);
R
12
is selected from H, alkyl, CO
2
R
6
, CONR
6
R
13
, OR
6
, SR
6
, SO
2
R
6
, SO
2
NR
6
R
13
and NR
6
R
13
;
R
13
is H, alkyl, aryl or arylalkyl;
A is N or CH;
B is N or CR
10
;
Z is O, CH(R
3
), CO, CS, CONR
12
or CSNR
12
;
X is selected from O, S, NR
12
, CO
2
, OCH(R
6
)CO
2
, SCH(R
6
)CO
2
, CH═C(halo)CO
2
, CH
2
CH(halo)CO
2
, CONH, OCH(R
6
)CONH, SCH(R
6
)CONH, CH═C(halo)CONH and CH
2
CH(halo)CONH when Z is CH(R
3
);
X is selected from CO, OCH(R
6
)CO, SCH(R
6
)CO, CH═C(halo)CO and CH
2
CH(halo)CO when Z is O;
X is selected from O, S, CO, OCH(R
6
), CH═C(halo), CH
2
CH(halo), CONH, OCH(R
6
)CONH, SCH(R
6
)CONH, CH═C(halo)CONH, CH
2
CH(halo)CONH and NR
12
when Z is CO, CS, CONR
12
or CSNR
12
; and
Q is selected from NR
7
COR
8
, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q14, Q15 and Q16 wherein
Q1 is 4,5,6,7-tetrahydrophthalimid-2-yl,
Q2 is 5,6,7,8-tetrahydro-1,2,4-triazolo[4, 3-a]pyridin-3(2H)-one-1-yl,
Q3 is 5,6,7,8-tetrahydro-1H,3H-[1,3,4]thiadiazolo[3,5-a]pyridazineimin-1-yl,
Q4 is 4,5,6,7-tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione-2-yl,
Q5 is 1,6,8-triazabicyclo[4,3,0]-nonane-7,9-dion-8-yl,
Q6 is 5-(1-methyethylidene)-2,4-oxazolidinedione-3-yl,
Q7 is 5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one-3-yl,
Q8 is 4-difluoromethyl-4, 5-dihydro-3-methyl- 1,2,4-triazol-5(1H)-one-1-yl,
Q9 is 2-methyl-1,2,4-oxadiazolidine-3,5-dione-4-yl,
Q10 is 4-chloro-1-methyl-5-difluoromethoxy-1H-pyrazol-3-yl,
Q11 is 4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl,
Q12 is 1-substituted-6-trifluoromethyl-2,4-pyrimidione-3-yl,
Q13 is 1-substituted-6-trifluoromethyl-1,3,5-triazine-2,4-dione-1-yl,
Q14 is 4,5-disubstituted-4,5-dihydro-1,2,4-triazine-3(2H)-one-2-yl,
Q15 is 4-substituted-1,2,4-triazine-3,5(2H,4H)-dione-2-yl and
Q16 is 5-methyl-6-oxo-4-(trifluoromethyl)-6H-pyridazin- 1-yl;
or the agronomically acceptable salts thereof
As used in the present invention, the term “aryl” is defined as a monocyclic or polycyclic ring selected from benzene, naphthalene, indene, anthracene, indacene, fluorene, acenaphthalene, phenanthrene and azulene.
“Heteroaryl” is defined as a monocyclic or polycyclic ring selected from furan, thiophene, pyrrole, isoxazole, oxazole, isothiazole, thiazole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, benzofuran, benzothiophene, indole, benzisoxazole, benzoxazole, benzisothiazole, benzothiazole, benzopyrazole, benzimidazole, benzotriazole, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, quinoline and isoquinoline.
The structures of the “Q” heterocyclic groups previously named are
where R
10
and R
11
are as previously defined.
The term “alkyl” includes both branched and straight chain alkyl groups. Typical alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like.
The term “cycloalkyl” refers to a cyclic aliphatic ring structure such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane and the like.
The term “haloalkyl” refers to an alkyl group substituted with one or more halo groups.
The term “halo” r

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