Herbicidal synergistic composition and method of weed control

Details Herbicidal synergistic composition and method of weed control Herbicidal synergistic composition and method of weed control

2000-09-18

2002-06-11

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S136000

Reexamination Certificate

active

06403531

ABSTRACT:

The present invention relates to a novel herbicidal synergistic composition comprising a combination of herbicidal active ingredients, which composition is suitable for selective weed control in crops of useful plants, for example in crops of cereals, cotton, soybeans, sugar beet, sugar cane, plantations crops, rape, maize and rice. The invention further relates to a method of controlling weeds in crops of useful plants and to the use of the novel composition for that purpose.
The compound of formula I
has herbicidal activity.
The following compounds are also known as herbicides and some of them are also available commercially:
compounds of formula II
A—SO
2
—NH—E  (II),
wherein A is the group A
1
and E is the group E
1
COOCH
3
(E
1
) or E
2
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 549 and 49;
compounds of formula III
wherein U—V is a group of the formula R
1
C═N, N═CR
1
, CONR
1
, R
1
NCO or R
1
C═CR
2
, wherein R
1
is —NHC
3
H
7
-(iso), —NHC(CH
3
)
2
CN, —NHC
4
H
9
-(tert), —NHC
2
H
5
,
W—Y is a group of the formula CR
2
═N, CONR
2
, NR
2
CO, CONR
3
or CR
2
═CR
3
, wherein R
2
is methyl, —Cl, —NH
2
, —NHC
3
H
7
-(iso) or —NHC
2
H
5
and
R
3
is —NHCH
3
or C
4
H
9
-(tert), and
R is —Cl, —SCH
3
, —C
4
H
9
-(tert), methoxy, hydroxy, N(CH
3
)
2
, CHF
2
or hydrogen; or
U—V—W—Y together form the group —C(CF
3
)═C(R
4
)—C(CH
2
—C
3
H
7
-(iso))═C(R
5
)—, wherein R
4
is —COSCH
3
or
and
R
5
is COOCH
3
or COSCH
3
,
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 32, 51, 565, 840, 740, 239, 956, 699, 959, 962, 974 and 375; compounds of formula IV
wherein n is 0 or 1,
R
6
is hydrogen, —CH
3
or —NH
2
,
R
7
is hydroxy, C
2
H
5
, Na
+
, —CH(CH
3
)
2
—CO
2
—CH═CH
2
, —C
4
H
9
-n or —CH
2
—CH
2
—O—N═C(CH
3
)
2
, and Q is the group
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 271, 888, 542, 541, 898, 441, 623, 471, 848 and 298, and from U.S. Pat. No. 5,183,492;
compounds of formula V
wherein R
8
is the group
3-trifluoromethylphenyl or phenyl,
R
9
and R
10
are each independently of the other hydrogen or methyl and
R
11
is methyl or the group
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 376, 490, 947 and 975;
compounds of formula VI
wherein X is —NH— or —NC
3
H
7
-(n),
R
12
is —C
3
H
7
-(n) or CH(C
2
H
5
)
2
, or X and R
12
together are cyano,
R
13
is 2-NO
2
or 3-Br,
R
14
4-CF
3
, 4-CH
3
or 4-OH,
R
15
6-NO
2
or 5-Br, and
R
16
is 3-CH
3
or 5-NH
2
,
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 1025, 779, 121 and 835;
compounds of formula VII
Z—N(R
17
)—R
18
  (VII),
wherein
Z is the group
or
R
17
is —CH(CH
3
)—CH
2
OCH
3
,
CH
2
OC
2
H
5
or —CH
2
OCH
3
, R
18
is —C(O)—CH
2
Cl or
R
17
and R
18
together are the group —C(O)—C(CH
3
)
2
—CH
2
—O— or
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 693, 10, 21 and 220, and from AGROW No. 247, 5.1. (1996) page 19 and U.S. Pat. No. 5,002,606;
compounds of formula VIII
wherein R
19
is hydrogen or —CH
2
—CH(CH
3
)—SC
2
H
5
,
R
20
is —C
2
H
5
, —C
3
H
7
-(n) or
and
X
a
is oxygen, NOC
2
H
5
or NOCH
2
—CH═CHCl (trans),
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 909, 214 and 577;
compounds of formula IX
wherein X
b
is chlorine or CH
3
SO
3
,
are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, page 767;
the compound of formula X
CH
3
—As(O)—(OH)
2
  (X),
and its salts, especially the monosodium and disodium salts, are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, page 683.
Surprisingly, it has now been found that a combination of two active ingredients in variable proportions, i.e. a combination of the active ingredient of formula I with one of the above-mentioned active ingredients of formulae II to X, has a synergistic effect that is capable of controlling, both pre-emergence and post-emergence, the majority of weeds occurring especially in crops of useful plants without significantly damaging the useful plants. According to the present invention, therefore, a novel synergistic composition for selective weed control is proposed that comprises as active ingredient, in addition to conventional inert formulation adjuvants, the compound of formula I
in admixture with a synergistically effective amount of at least one compound from the substance classes of formula II
A—SO
2
—NH—E  (II),
wherein A is the group A
1
and E is the group E
1
COOCH
3
(E
1
) or E
2
of the formula III
wherein U—V is a group of the formula R
1
C═N, N═CR
1
, CONR
1
, R
1
NCO or R
1
C═CR
2
, wherein
R
1
is —NHC
3
H
7
-(iso), —NHC(CH
3
)
2
CH, —NHC
4
H
9
-(tert), —NHC
2
H
5
, —SCH
3
,
W—Y is a group of the formula CR
2
═N, CONR
2
, NR
2
CO, CONR
3
or CR
2
═CR
3
, wherein
R
2
is methyl, —Cl, —NH
2
, —NHC
3
H
7
-(iso) or —NHC
2
H
5
and
R
3
is —NHCH
3
or C
4
H
9
-(tert), and
R is —Cl, —SCH
3
, —C
4
H
9
-(tert), methoxy, hydroxy, N(CH
3
)
2
, CHF
2
or hydrogen; or
U—V—W—Y together form the group —C(CF
3
)═C(R
4
)—C(CH
2
—C
3
H
7
-(iso))═C(R
5
)—, wherein R
4
is —COSCH
3
or
and
R
5
is COOCH
3
or COSCH
3
;
of formula IV
wherein n is 0 or 1, R
6
is hydrogen, —CH
3
or —NH
2
,
R
7
is hydroxy, C
2
H
5
, Na
+
, —CH(CH
3
)
2
—CO
2
—CH═CH
2
, —C
4
H
9
-n or —CH
2
—CH
2
—O—N═C(CH
3
)
2
, and
Q is the group
of formula V
wherein R
8
is the group
3-trifluoromethylphenyl or phenyl,
R
9
and R
10
are each independently of the other hydrogen or methyl and
R
11
is methyl or the group
of formula VI
wherein
X is —NH— or —NC
3
H
7
-(n),
R
12
is —C
3
H
7
-(n) or CH(C
2
H
5
)
2
, or X and R
12
together are cyano,
R
13
is 2-NO
2
or 3-Br,
R
14
4-CF
3
, 4-CH
3
or 4-OH,
R
15
6-NO
2
or 5-Br, and
R
16
is 3-CH
3
or 5-NH
2
;
of formula VII
Z—N(R
17
)—R
18
  (VII),
wherein
R
17
is —CH(CH
3
)—CH
2
OCH
3
,
—CH
2
OC
2
H
5
or —CH
2
OCH
3
,
R
18
is —C(O)—CH
2
Cl or R
17
and R
18
together are the group —C(O)—C(CH
3
)
2
—CH
2
—O— or
of formula VIII
wherein R
19
is hydrogen or —CH
2
—CH(CH
3
)—SC
2
H
5
,
R
20
is —C
2
H
5
, —C
3
H
7
-(n) or
and
X
a
is oxygen, NOC
2
H
5
or NOCH
2
—CH═CHCl (trans); of formula IX
wherein X
b
is chlorine or CH
3
SO
3
;
and of formula X
CH
3
—As(O)—(OH)
2
  (X),
and salts thereof.
The sulfonylurea compound of formula F
1
which corresponds to the salt of formula I Is known, for example, from EP-A-0 103 453. By reaction with suitable salt-forming agents the compound of formula F
1
can be converted into the compound of formula I in a conventional manner known per se. Such salt-forming agents are, in principle, all bases that are capable of abstracting the acid hydrogen atom in the SO
2
—NH—CO— grouping. There have been found to be especially advantageous in this connection hydrides, hydroxides, alcoholates, hydrogen carbonates and carbonates of sodium. The reaction of the compound of formula F
1
with the bases to form the compound of formula I is carried out in a manner known per se, preferably in protic or aprotic solvents at room temperature or elevated temperature, in which reaction crown ethers and/or phase transfer catalysts may be present as is described, for example, in J. March, Advanced Org. Chem., John Wiley and Sons, 4th Edition, 1992: Phase Transfer Catalysis, page 362. For example, the compound of formula I can be obtained in good yields by simply stirring the compound of formula F
1
with aqueous sodium hydroxide solution at room temperature. Such methods are described, for example, in WO 97/41112.
According to the invention, preference is given to compositions that comprise the compound of formula I and at least one co

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