U.S. patent application number 10/144498 was filed with the patent office on 2003-04-10 for herbicidal synergistic composition and method of weed control.
Invention is credited to Hudetz, Manfred, Ruegg, Willy.
Application Number | 20030069136 10/144498 |
Document ID | / |
Family ID | 4181048 |
Filed Date | 2003-04-10 |
United States Patent
Application |
20030069136 |
Kind Code |
A1 |
Ruegg, Willy ; et
al. |
April 10, 2003 |
Herbicidal synergistic composition and method of weed control
Abstract
A herbicidal composition comprising, in addition to conventional
inert formulation adjuvants, the compound of formula I 1 in
admixture with a synergistically effective amount of at least one
active ingredient from the substance classes of formula II 2
wherein X.sub.0 is chlorine or CH.sub.3SO.sub.3; and of formula X
CH.sub.3--As(O)--(OH).sub.2 (X), wherein the substituents are as
defined in claim 1.
Inventors: |
Ruegg, Willy;
(Gipf-Oberfrick, CH) ; Hudetz, Manfred;
(Rheinfelden, CH) |
Correspondence
Address: |
SYNGENTA CROP PROTECTION , INC.
PATENT AND TRADEMARK DEPARTMENT
410 SWING ROAD
GREENSBORO
NC
27409
US
|
Family ID: |
4181048 |
Appl. No.: |
10/144498 |
Filed: |
May 13, 2002 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10144498 |
May 13, 2002 |
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09664111 |
Sep 18, 2000 |
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6403531 |
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09664111 |
Sep 18, 2000 |
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09013012 |
Jan 26, 1998 |
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6180563 |
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Current U.S.
Class: |
504/133 ;
504/136 |
Current CPC
Class: |
A01N 47/36 20130101;
A01N 47/36 20130101; A01N 55/02 20130101; A01N 47/30 20130101; A01N
43/80 20130101; A01N 43/70 20130101; A01N 43/58 20130101; A01N
43/54 20130101; A01N 37/34 20130101; A01N 37/22 20130101; A01N
37/18 20130101; A01N 47/36 20130101; A01N 2300/00 20130101 |
Class at
Publication: |
504/133 ;
504/136 |
International
Class: |
A01N 043/64; A01N
043/60; A01N 057/00 |
Foreign Application Data
Date |
Code |
Application Number |
Jan 28, 1997 |
CH |
178/97 |
Claims
What is claimed is:
1. A herbicidal synergistic composition which comprises, in
addition to conventional inert formulation adjuvants, the compound
of formula I 52in admixture with a synergistically effective amount
of at least one compound from the substance classes of formula II
A-SO.sub.2--NH-E (II), wherein A is the group A.sub.1 53and E is
the group E.sub.1 COOC.sub.2H.sub.5 (E.sub.1) or E.sub.2 of formula
III 54wherein U--V is a group of the formula R.sub.1C.dbd.N,
N.dbd.CR.sub.1, CONR.sub.1, R.sub.1NCO or R.sub.1C.dbd.CR.sub.2,
wherein R.sub.1 is --NHC.sub.3H.sub.7-(iso),
--NHC(CH.sub.3).sub.2CN, --NHC.sub.4H.sub.9-(tert),
--NHC.sub.2H.sub.5, --SCH.sub.3, 55W--Y is a group of the formula
CR.sub.2.dbd.N, CONR.sub.2, NR.sub.2CO, CONR.sub.3 or
CR.sub.2.dbd.CR.sub.3, wherein R.sub.2 is methyl, --Cl, --NH.sub.2,
--NHC.sub.3H.sub.7-(iso) or --NHC.sub.2H.sub.5 and R.sub.3 is
--NHCH.sub.3 or C.sub.4H.sub.9-(tert), and R is --Cl, --SCH.sub.3,
--C.sub.4H.sub.9-(tert), methoxy, hydroxy, N(CH.sub.3).sub.2,
CHF.sub.2 or hydrogen; or U--V--W--Y together form the group
--C(CF.sub.3).dbd.C(R.sub.4)--C(CH.sub.2--C.sub.3H.sub.7-(iso)).dbd.C(R.s-
ub.5)--, wherein R.sub.4 is --COSCH.sub.3 or 56and R.sub.5 is
COOCH.sub.3 or COSCH.sub.3; of formula IV 57wherein n is 0 or 1,
R.sub.6 is hydrogen, --CH.sub.3 or --NH.sub.2, R.sub.7 is hydroxy,
C.sub.2H.sub.5, Na.sup.+,
--CH(CH.sub.3).sub.2--CO.sub.2--CH.dbd.CH.sub.2, --C.sub.4H.sub.9-n
or --CH.sub.2--CH.sub.2--O--N.dbd.C(CH.sub.3).sub.2, and Q is the
group 58of formula V wherein R.sub.8 is the group
593-trifluoromethylphenyl or phenyl, R.sub.9 and R.sub.10 are each
independently of the other hydrogen or methyl and R.sub.11 is
methyl or the group 60of formula VI 61wherein X is --NH--or
--NC.sub.3H.sub.7-(n), R.sub.12 is --C.sub.3H.sub.7-(n) cr
CH(C.sub.2H.sub.5).sub.2, or X and R.sub.12 together are cyano,
R.sub.13 is 2-NO.sub.2 or 3-Br, R.sub.14 4-CF.sub.3, 4-CH.sub.3 or
4-OH, R.sub.15 6-NO.sub.2 or 5-Br, and R.sub.16 is 3-CH.sub.3 or
5-NH.sub.2; of formula VII Z-N(R.sub.17)--R.sub.18 (VII), wherein
62R.sub.18 is --C(O)--CH.sub.2Cl or R.sub.17 and R.sub.18 together
are the group --C(O)--C(CH.sub.3).sub.2--CH.sub.2--O--or 63of
formula VIII 64wherein R.sub.19 is hydrogen or
--CH.sub.2--CH(C.sub.3)--SC.sub.2H.sub.5, R.sub.20 is
--C.sub.2H.sub.5, --C.sub.3H.sub.7-(n) or 65X.sub.a is oxygen,
NOC.sub.2H.sub.5 or NOCH.sub.2--CH.dbd.CHCl (trans); of formula IX
66wherein X.sub.b is chlorine or CH.sub.3SO.sub.3; and of formula X
CH.sub.3--As(O)--(OH).sub.2 (X), and salts thereof.
2. A herbicidal composition according to claim 1, which comprises
the compound of formula I and at least one compound selected from
the compounds ametryn, atrazine, hexazinone, asulam, diuron, 2,4-D,
halosulfuron and the compound of formula IV wherein Q is Q.sub.1,
R.sub.7 is --C(CH.sub.3).sub.2--C(O)O--CH.sub.2CH.dbd.CH.sub.2 and
n is 0.
3. A herbicidal composition according to claim 2, which comprises
the compound of formula I and at least one compound selected from
the compounds ametryn, atrazine, hexazinone and asulam.
4. A herbicidal composition according to claim 1, which comprises
the compound of formula I and at least one compound selected from
the compounds fluometuron, prometryn, metolachlor,
.alpha.-metolachlor, norflurazon, pyrithiobac-sodium, DSMA, MSMA,
trifluralin, pendimethalin, bromoxynil, glyphosate, glufosinate and
clomazone.
5. A herbicidal composition according to claim 4, which comprises
the compound of formula I and at least one compound selected from
the compounds fluometuron, prometryn, metolachlor,
.alpha.-metolachlor, norflurazon, pyrithiobac-sodium, MSMA and
DSMA.
6. A herbicidal composition according to claim 1, wherein the
component of formula I is present in a weight ratio of from 1:100
to 1000:1 in relation to the component of formula II, III, IV, V,
VI, VII, VIII, IX or X.
7. A method of controlling undesired plant growth in crops of
useful plants, which comprises allowing a herbicidally effective
amount of a composition according to claim 1 to act on the
cultivated plant or the locus thereof.
8. A method according to claim 7, wherein the cultivated plant is
cotton or sugar cane.
9. A method according to claim 7, wherein the crops of useful
plants are treated with said composition at rates of application
corresponding to from 0.008 to 5 kg/ha total amount of active
ingredients per hectare.
Description
HERBICIDAL SYNERGISTIC COMPOSITION AND METHOD OF WEED CONTROL
[0001] 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.
[0002] The compound of formula I 3
[0003] has herbicidal activity.
[0004] The following compounds are also known as herbicides and
some of them are also available commercially:
[0005] compounds of formula II
A-SO.sub.2--NH-E (II),
[0006] wherein A is the group A.sub.1 4
[0007] and E is the group E.sub.1 COOC.sub.2H.sub.5 (E.sub.1) or
5
[0008] are known, for example, from The Pesticide Manual, 10th ed.
British Crop Protection Council 1994, pages 549 and 49;
[0009] compounds of formula III 6
[0010] wherein U--V is a group of the formula R.sub.1C.dbd.N,
N.dbd.CR.sub.1, CONR.sub.1, R.sub.1NCO or R.sub.1C.dbd.CR.sub.2,
wherein R.sub.1 is --NHC.sub.3H.sub.7-(iso),
--NHC(CH.sub.3).sub.2CN, --NHC.sub.4H.sub.9-(tert),
--NHC.sub.2H.sub.5, --SCH.sub.3, 7
[0011] W--Y is a group of the formula CR.sub.2.dbd.N, CONR.sub.2,
NR.sub.2CO, CONR.sub.3 or CR.sub.2.dbd.CR.sub.3,
[0012] wherein R.sub.2 is methyl, --Cl, --NH.sub.2,
--NHC.sub.3H.sub.7-(iso) or --NHC.sub.2H.sub.5 and R.sub.3 is
--NHCH.sub.3 or C.sub.4H.sub.9-(tert), and R is --Cl, --SCH.sub.3,
--C.sub.4H.sub.9-(tert), methoxy, hydroxy, N(CH.sub.3).sub.2,
CHF.sub.2 or hydrogen; or U--V--W--Y together form the group
--C(CF.sub.3).dbd.C(R.sub.4)--C(CH.sub.2-C.sub.3H.sub.7-(iso)).dbd.C(R.su-
b.5)--, wherein R.sub.4 is --COSCH.sub.3 or 8
[0013] and R.sub.5 is COOCH.sub.3 or COSCH.sub.3,
[0014] 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;
[0015] compounds of formula IV 9
[0016] wherein n is 0 or 1,
[0017] R.sub.6 is hydrogen, --CH.sub.3 or --NH.sub.2,
[0018] R.sub.7 is hydroxy, C.sub.2H.sub.5, Na.sup.+,
--CH(CH.sub.3).sub.2--CO.sub.2--CH.dbd.CH.sub.2, --C.sub.4H.sub.9-n
or
[0019] --CH.sub.2--CH.sub.2--O--N.dbd.C(CH.sub.3).sub.2, and Q is
the group 10
[0020] 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 US-A-5 183 492;
[0021] compounds of formula V
[0022] wherein R.sub.8 is the group 11
[0023] 3-trifluoromethylphenyl or phenyl,
[0024] R.sub.9 and R.sub.10 are each independently of the other
hydrogen or methyl and R.sub.11 is methyl or the group 12
[0025] are known, for example, from The Pesticide Manual, 10th ed.
British Crop Protection Council 1994, pages 376, 490, 947 and
975;
[0026] compounds of formula VI 13
[0027] wherein X is --NH-- or --NC.sub.3H.sub.7-(n),
[0028] R.sub.12 is --C.sub.3H.sub.7-(n) or
CH(C.sub.2H.sub.5).sub.2, or X and R.sub.12 together are cyano,
[0029] R.sub.13 is 2-NO.sub.2 or 3-Br,
[0030] R.sub.14 4-CF.sub.3, 4-CH.sub.3 or 4-OH,
[0031] R.sub.15 6-NO.sub.2 or 5-Br, and
[0032] R.sub.16 is 3-CH.sub.3 or 5-NH.sub.2,
[0033] are known, for example, from The Pesticide Manual, 10th ed.
British Crop Protection Council 1994, pages 1025, 779, 121 and
835;
[0034] compounds of formula VII
Z-N(R.sub.17)--R.sub.18 (VII),
[0035] wherein 14
[0036] 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 US-A-5 002 606;
[0037] compounds of formula VIII 15
[0038] wherein R.sub.19 is hydrogen or
--CH.sub.2--CH(CH.sub.3)--SC.sub.2H- .sub.5, R.sub.20 is
--C.sub.2H.sub.5, --C.sub.3H.sub.7-(n) or 16
[0039] X.sub.a is oxygen, NOC.sub.2H.sub.5 or
NOCH.sub.2--CH.dbd.CHCl (trans), are known, for example, from The
Pesticide Manual, 10th ed. British Crop Protection Council 1994,
pages 909, 214 and 577;
[0040] compounds of formula IX 17
[0041] wherein X.sub.b is chlorine or CH.sub.3SO.sub.3, are known,
for example, from The Pesticide Manual, 10th ed. British Crop
Protection Council 1994, page 767;
[0042] the compound of formula X
CH.sub.3--As(O)--(OH).sub.2 (X),
[0043] 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.
[0044] 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
18
[0045] in admixture with a synergistically effective amount of at
least one compound from the substance classes of formula II
A-SO.sub.2--NH-E (II),
[0046] wherein A is the group A.sub.1 19
[0047] and E is the group E.sub.1 COOC.sub.2H.sub.5 (E.sub.1) or
E.sub.2 of formula III 20
[0048] wherein U--V is a group of the formula R.sub.1C.dbd.N,
N.dbd.CR.sub.1, CONR.sub.1, R.sub.1NCO or R.sub.1C.dbd.CR.sub.2,
wherein R.sub.1 is --NHC.sub.3H.sub.7-(iso),
--NHC(CH.sub.3).sub.2CN, --NHC.sub.4H.sub.9-(tert),
--NHC.sub.2H.sub.5, 21
[0049] W--Y is a group of the formula CR.sub.2.dbd.N, CONR.sub.2,
NR.sub.2CO, CONR.sub.3 or CR.sub.2.dbd.CR.sub.3, wherein R.sub.2 is
methyl, --Cl, --NH.sub.2, --NHC.sub.3H.sub.7-(iso) or
--NHC.sub.2H.sub.5 and R.sub.3 is --NHCH.sub.3 or
C.sub.4H.sub.9-(tert), and R is --Cl, --SCH.sub.3,
--C.sub.4H.sub.9-(tert), methoxy, hydroxy, N(CH.sub.3).sub.2,
CHF.sub.2 or hydrogen; or U--V--W--Y together form the group
--C(CF.sub.3).dbd.C(R.sub.4)--C(CH.sub.2-C.sub.3H.sub.7-(iso)).dbd.-
C(R.sub.5)--, wherein R.sub.4 is --COSCH.sub.3 or 22
[0050] and R.sub.5 is COOCH.sub.3 or COSCH.sub.3; of formula IV
23
[0051] wherein n is 0 or 1, R.sub.6 is hydrogen, --CH.sub.3 or
--NH.sub.2,
[0052] R.sub.7 is hydroxy, C.sub.2H.sub.5, Na.sup.+,
--CH(CH.sub.3).sub.2-CO.sub.2-CH.dbd.CH.sub.2, --C.sub.4H.sub.9-n
or --CH.sub.2--CH.sub.2--O--N.dbd.C(CH.sub.3).sub.2, and Q is the
group 24
[0053] of formula V
[0054] wherein R.sub.8 is the group 25
[0055] 3-trifluoromethylphenyl or phenyl,
[0056] R.sub.9 and R.sub.10 are each independently of the other
hydrogen or methyl and R.sub.11 is methyl or the group 26
[0057] of formula VI 27
[0058] wherein
[0059] X is --NH-- or --NC.sub.3H.sub.7-(n),
[0060] R.sub.12 is --C.sub.3H.sub.7-(n) or
CH(C.sub.2H.sub.5).sub.2, or X and R.sub.12 together are cyano,
[0061] R.sub.13 is 2-NO.sub.2 or 3-Br,
[0062] R.sub.14 4-CF.sub.3, 4-CH.sub.3 or 4-OH,
[0063] R.sub.15 6-NO.sub.2 or 5-Br, and
[0064] R.sub.16 is 3-CH.sub.3 or 5-NH.sub.2; of formula VII
Z-N(R.sub.17)--R.sub.18 (VII),
[0065] wherein 28
[0066] R.sub.18 is --C(O)--CH.sub.2Cl or R.sub.17 and R.sub.18
together are the group --C(O)--C(CH.sub.3).sub.2--CH.sub.2-O-- or
29
[0067] of formula VIII 30
[0068] wherein R.sub.19 is hydrogen or
--CH.sub.2--CH(CH.sub.3)--SC.sub.2H- .sub.5,
[0069] R.sub.20 is --C.sub.2H.sub.5, --C.sub.3H.sub.7-(n) or 31
[0070] X.sub.a is oxygen, NOC.sub.2H.sub.5 or
NOCH.sub.2--CH.dbd.CHCl (trans); of formula IX 32
[0071] wherein X.sub.b is chlorine or CH.sub.3SO.sub.3; and of
formula X
CH.sub.3--As(O)--(OH).sub.2 (X),
[0072] and salts thereof.
[0073] The sulfonylurea compound of formula F.sub.1 33
[0074] 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.sub.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.sub.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.sub.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.sub.1 with aqueous sodium hydroxide solution at room
temperature. Such methods are described, for example, in WO
97/41112.
[0075] According to the invention, preference is given to
compositions that comprise the compound of formula I and at least
one compound selected from the compounds ametryn, atrazine,
hexazinone, asulam, diuron, 2,4-D, halosulfuron and the compound of
formula IV wherein Q is Q.sub.1, R.sub.7 is
--C(CH.sub.3).sub.2--C(O)O--CH.sub.2CH.dbd.CH.sub.2 and n is 0. Of
those compositions, special preference is given to those that
comprise the compound of formula I and at least one compound
selected from the compounds ametryn, atrazine, hexazinone and
asulam. Prominence is to be given also to compositions that
comprise the compound of formula I and at least one compound
selected from the compounds fluometuron, prometryn, metolachlor,
.alpha.-metolachlor, norflurazon, pyrithiobac-sodium, DSMA, MSMA,
trifluralin, pendimethalin, bromoxynil, glyphosate, glufosinate and
clomazone. Of those, special mention is to be made of those
compositions according to the invention that comprise the compound
of formula I and at least one compound selected from the compounds
fluometuron, prometryn, metolachlor, .alpha.-metolachlor,
norflurazon, pyrithiobac-sodium, MSMA and DSMA
[0076] When R.sub.6 in formula IV is other than hydrogen, the
R-enantiomer of that formula is especially preferred.
[0077] Compounds of formula II that are especially suitable for use
in the composition according to the invention are those wherein
[0078] a) A is A.sub.1 and E is E.sub.1 (common name: asulam)
and
[0079] b) A is A.sub.2 and E is E.sub.2 (common name:
halosulfuron).
[0080] Compounds of formula IlI that are especially suitable for
use in the composition according to the invention are listed in
Table 1:
1TABLE 1 Preferred compounds of formula III: (III) 34 comp No. U-V
W-Y R R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 1.01 R.sub.1C.dbd.N
R.sub.2C.dbd.N SCH.sub.3 NHC.sub.2H.sub.5 NHC.sub.3H.sub.7- -- --
-- (iso) 1.02 R.sub.1C.dbd.N R.sub.2C.dbd.N Cl NHC.sub.2H.sub.5
NHC.sub.3H.sub.7- -- -- -- (iso) 1.03 CONR.sub.1 CONR.sub.2
N(CH.sub.3).sub.2 cyclohexyl CH.sub.3 -- -- -- 1.04 R.sub.1C.dbd.N
R.sub.2C.dbd.N SCH.sub.3 NHC.sub.3H.sub.7- NHC.sub.3H.sub.7- -- --
-- (iso) (iso) 1.05 R.sub.1NCO R.sub.2C.dbd.CR.sub.3 H 3-trifluoro-
Cl NHCH.sub.3 -- -- methyl- phenyl 1.06 R.sub.1C.dbd.N
R.sub.2C.dbd.N Cl NHC.sub.2H.sub.5 NHC(CH.sub.3).sub.2-- -- -- --
CN 1.07 R.sub.1C.dbd.CR.sub.2 CONR.sub.3 OH CH.sub.3 Cl
C.sub.4H.sub.9-(tert) -- -- 1.08 N.dbd.CR.sub.1 R.sub.2NCO
C.sub.4H.sub.9-(tert) SCH.sub.3 NH.sub.2 -- -- -- 1.09
R.sub.1C.dbd.N R.sub.2C.dbd.N OCH.sub.3 NHC.sub.2H.sub.5
NHC.sub.4H.sub.9- -- -- -- (tert) 1.10 R.sub.1C.dbd.N
R.sub.2C.dbd.N SCH.sub.3 NHC.sub.2H.sub.5 NHC.sub.4H.sub.9- -- --
-- (tert) 1.11 --C(CF.sub.3).dbd.C(R.sub.4)--C(CH.sub-
.2--C.sub.3H.sub.7-(iso)).dbd.C(R.sub.5)-- CHF.sub.2 -- -- -- -- 35
COOCH.sub.3 1.12 --C(CF.sub.3).dbd.C(R.sub.4)--C(CH.sub.2-
--C.sub.3H.sub.7-(iso)).dbd.C(R.sub.5)-- CHF.sub.2 -- -- -- --
COSCH.sub.3 COSCH.sub.3 The compounds of Table 1 are known by the
following names: Comp. No. Common name 1.01 ametryn 1.02 atrazine
1.03 hexazinone 1.04 prometryn 1.05 norflurazon 1.06 cyanazine 1.07
terbacil 1.08 metribuzin 1.09 terbumeton 1.10 terbutryn 1.11
thiazopyr 1.12 dithiopyr
[0081] Compounds of formula IV that are especially suitable for use
in the composition according to the invention are listed in Table
2:
2TABLE 2 Preferred compounds of formula IV (IV) 36 Comp. No. Q
R.sub.6 R.sub.7 n common name 2.01 Q.sub.1 --
--C(CH.sub.3).sub.2--C(O)O--CH- .sub.2CH.dbd.CH.sub.2 0 -- 2.02
Q.sub.2 H H (and the salts) 1 2,4-D 2.03 Q.sub.3 -- Na 0
pyrithiobac-sodium 2.04 Q.sub.4 H H (and the salts) 1 glyphosate
2.05 Q.sub.5 NH.sub.2 H (and the salts) 1 glufosinate 2.06 Q.sub.6
CH.sub.3(R) C.sub.2H.sub.5 1 quizalofop 2.07 Q.sub.7 CH.sub.3(R)
C.sub.2H.sub.5 1 fenoxaprop-P 2.08 Q.sub.9 CH.sub.3 C.sub.2H.sub.5
1 lactofen 2.09 Q.sub.8 CH.sub.3(R) C.sub.4H.sub.9-(n) 1 fluazifop
2.10 Q.sub.6 CH.sub.3(R) C.sub.2H.sub.4ON.dbd.C(CH.sub.3)--CH.sub.3
1 propaquizafop 2.11 Q.sub.10 -- H (and the salts) 0 dicamba
[0082] Compounds of formula V that are especially suitable for use
in the composition according to the invention are listed in Table
3:
3TABLE 3 Preferred compounds of formula V (V) 37 Comp. No. R.sub.8
R.sub.9 R.sub.10 R.sub.11 common name 3.01 38 H CH.sub.3 CH.sub.3
diuron 3.02 3-trifluoromethylphenyl H CH.sub.3 CH.sub.3 fluometuron
3.03 39 CH.sub.3 H CH.sub.3 tebuthiuron 3.04 phenyl H H 40
thidiazuron
[0083] Compounds of formula VI that are especially suitable for use
in the composition according to the invention are listed in Table
4:
4TABLE 4 Preferred compounds of formula VI: (VI) 41 Comp. No. X
R.sub.12 R.sub.13 R.sub.14 R.sub.15 R.sub.16 common name 4.01
N--C.sub.3H.sub.7-(n) C.sub.3H.sub.7(n) 2-NO.sub.2 4-CF.sub.3
6-NO.sub.2 H trifluralin 4.02 NH CH(C.sub.2H.sub.5).sub.2
2-NO.sub.2 4-CH.sub.3 6-NO.sub.2 3-CH.sub.3 pendimethalin 4.03 CN
3-Br 4-OH 5-Br H bromoxinil 4.04 N--C.sub.3H.sub.7-(n)
C.sub.3H.sub.7-(n) 2-NO.sub.2 4-CF.sub.3 6-NO.sub.2 5-NH.sub.2
prodiamine
[0084] Compounds of formula VII that are especially suitable for
use in the composition according to the invention are listed in
Table 5:
5TABLE 5 Preferred compounds of formula VII:
Z--N(R.sub.17)--R(.sub.18) (VII) Comp. No. Z R.sub.17 R.sub.18
common name 5.01 42 --CH(CH.sub.3)--CH.sub.2OC- H.sub.3
--C(O)--CH.sub.2Cl metolachlor 5.02 43 44 --C(O)--CH.sub.2Cl
.alpha.-metolachlor 5.03 45 --CH.sub.2OC.sub.2H.sub.5
--C(O)--CH.sub.2Cl acetochlor 5.04 46 --CH.sub.2OCH.sub.3
--C(O)--CH.sub.2Cl alachlor 5.05 47
--C(O)--C(CH.sub.3).sub.2--CH.sub.2--O-- clomazone 5.06 48 49
azafenidine
[0085] Compounds of formula VIII that are especially suitable for
use in the composition according to the invention are listed in
Table 6:
6TABLE 6 Preferred compounds of formula VIII: (VIII) 50 Comp. No.
X.sub.a R.sub.19 R.sub.20 common name 6.01 NOC.sub.2H.sub.5
--CH.sub.2--CH(CH.sub.3)- -- --C.sub.3H.sub.7-(n) sethoxydim
SC.sub.2H.sub.5 6.02 NOCH.sub.2--CH.dbd.CHCl
--CH.sub.2--CH(CH.sub.3)-- --C.sub.2H.sub.5 clethodim (trans)
SC.sub.2H.sub.5 6.03 O H 51 sulcotrione
[0086] The monosodium salt of the compound of formula X is known by
the name MSMA. The disodium salt of the compound of formula X is
known by the name DSMA. The compound of formula IX wherein X is
chlorine is known by the name paraquat.
[0087] It is extremely surprising that the combination of the
active ingredient of formula I with an active ingredient of formula
II, III, IV, V, VI, VII, VIII, IX or X surpasses the additive
action on the weeds to be controlled that is to be expected in
principle, and thus broadens the range of action of both active
ingredients especially in two respects: Firstly, the rates of
application of the individual compounds I and II, III, IV, V, VI,
VII, VIII, IX and X are reduced while a good level of action is
maintained. Secondly, the composition according to the invention
achieves a high degree of weed control even in cases where the
compounds individually, when used at low rates of application, have
become no longer useful from an agronomic standpoint. The result of
this is a considerable broadening of the weed spectrum and an
additional increase in selectivity for crops of useful plants, as
is necessary and desirable in case of inadvertent overdosage of the
active ingredient. Furthermore, while maintaining outstanding
control of weeds in useful plants, the composition according to the
invention permits a greater flexibility with regard to subsequent
crops. In addition, the onset of action of the compound of formula
I can be accelerated in the presence of a mixing partner of formula
II, III, IV, V, VI, VII, VIII, IX or X.
[0088] The herbicide mixture according to the invention can be used
against a large number of agronomically important weeds, such as
Stellaria, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium,
Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus,
Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon,
Sida, Xanthium, Amaranthus, Chenopodium, lpomoea, Chrysanthemum,
Galium, Viola and Veronica. The compositions according to the
invention are suitable for all the methods of application usual in
agriculture, such as pre-emergence application, post-emergence
application and seed dressing. The herbicide mixture according to
the invention is suitable especially for weed control in crops of
useful plants, such as cereals, rape, sugar beet, sugar cane,
plantation crops (cotton), rice, maize and soybeans, more
especially in crops of sugar cane and cotton (especially
post-emergence application), and also for non-selective weed
control.
[0089] The compositions according to the invention are especially
suitable for controlling the following weeds in crops of sugar
cane: Erigeron canadensis, Convolvulus arvensis, Sorghum halepense,
Imperata cylindrica, Cynodon dactylon, Commenlina benghalensis,
Cyperus rotundus, Euphorbia heterophylla, Amaranthus retoflexus,
lpomoea hederacea, Brachiaria plantaginea, Digitaria sanguinalis,
Eleusine indica, Panicum miliaceum and Setaria faberi. The
compositions according to the invention are especially suitable for
controlling the following weeds in crops of cotton: Cyperus
rotundus, Sorghum bicolor, Digitaria sanguinalis, Echinochloa crus
galli, Eleusine indica, Panicum dichotomiflorum, Setaria faberi,
Brachiaria plantaginea, Abutilon, Amaranthus retoflexus, Cassia
obtusifolia, Chenopodium album, lpomoea hederacea, Sesbania
exaltata and Xanthium canadense. Furthermore, compositions that
comprise the compound of formula I and at least one herbicide
selected from dithiopyr, prodiamine and simazine are especially
suitable for use in lawns. The compound of formula I in combination
with flazasulfuron (known from The Pesticide Manual, 9th ed., page
397) and isoxaflutole (known from BRIGHTON CROP PROTECTION
CONFERENCE--Weeds--1995, Proceedings Volume 1, pages 35-42) also
exhibits a synergistic herbicidal action, especially in sugar cane
and lawns. Generally good action is also exhibited by a synergistic
mixture consisting of the active ingredient of formula I and
azafenidine (known from AGROW, No. 261, Aug. 2nd, 1996, page 23).
Crops are also to be understood as including those which have been
made tolerant towards herbicides or classes of herbicides by
conventional breeding or genetic engineering techniques, for
example maize, soybeans, cotton or sugar cane that is tolerant
towards glyphosate, glufosinate, bromoxynil and ALS-inhibitors,
such as sulfonylureas (chlorimuron, thifensulfuron), imidazolinone
(imazethapyr) or mixtures of those compounds.
[0090] The active ingredient combination according to the invention
comprises the active ingredient of formula I and the active
ingredient of formula II, III, IV, V, VI, VII, VIII, IX or X in any
desired mixing ratio, usually with an excess of the one component
over the other. Preferred mixing ratios between the active
ingredient of formula I and the mixing partners of formula II, III,
IV, V, VI, VII, VIII, IX or X are from 1:1 to 1:350, especially
from 1:5 to 1:70. The rate of application can vary within a wide
range and depends on the nature of the soil, the type of
application (pre- or post-emergence; seed dressing; application to
the seed furrow; no tillage application), on the cultivated plant,
the weed to be controlled, the prevailing climatic conditions and
on other factors determined by the type of application, the time of
application and the target crop. In general, the active ingredient
mixture according to the invention may be used at a rate of
application of from 0.008 to 5 kg/ha, especially from 0.3 to 2
kg/ha active ingredient mixture. The mixtures of the compound of
formula I with the compounds of formula II, III, IV, V, VI, VII,
VIII, IX or X can be used in unmodified form, i.e. as obtainable
from synthesis, but are preferably formulated in customary manner
with the adjuvants conventionally employed in formulation
technology, such as solvents, solid carriers or surfactants, into
e.g. directly sprayable or dilutable solutions, wettable powders,
soluble powders, dusts, granules or microcapsules. As with the
nature of the compositions, the methods of application, such as
spraying, atomising, dusting, wetting, scattering or pouring, are
chosen in accordance with the intended objectives and the
prevailing circumstances. The formulations, i.e. the compositions,
preparations or mixtures comprising the compounds (active
ingredients) of formulae I and II, III, IV, V, VI, VII, VIII, IX or
X and, where appropriate, one or more solid or liquid formulation
adjuvants, are prepared in a manner known per se, e.g. by
homogeneously mixing and/or grinding the active ingredients with
the formulation adjuvants, e.g. solvents or solid carriers. In
addition, surface-active compounds (surfactants) can also be used
in the preparation of the formulations.
[0091] Suitable solvents are: aromatic hydrocarbons, preferably the
fractions containing 8 to 12 carbon atoms, such as xylene mixtures
or substituted naphthalenes, phthalates, such as dibutyl or dioctyl
phthalate, aliphatic hydrocarbons, such as cyclohexane, or
paraffins, alcohols and glycols and their ethers and esters, such
as ethanol, ethylene glycol, ethylene glycol monomethyl or
monoethyl ether, ketones, such as cyclohexanone, strongly polar
solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or
N,N-dimethylformamide, and also vegetable oils or epoxidised
vegetable oils, such as epoxidised coconut oil or soybean oil, and
water. The solid carriers used e.g. for dusts and dispersible
powders are normally natural mineral fillers, such as calcite,
talcum, kaolin, montmorillonite or attapulgite. In order to improve
the physical properties of the formulation it is also possible to
add highly dispersed silicic acid or highly dispersed absorbent
polymers. Suitable granulated adsorptive carriers are porous types,
for example pumice, broken brick, sepiolite or bentonite; and
suitable non-sorbent carriers are, for example, calcite or sand. In
addition, a great number of pregranulated materials of inorganic or
organic nature can be used, such as, especially, dolomite or
pulverised plant residues. Depending on the nature of the compound
of formula I to be formulated, suitable surface-active compounds
are non-ionic, cationic and/or anionic surfactants and mixtures of
surfactants having good emulsifying, dispersing and wetting
properties. Both so-called water-soluble soaps and water-soluble
synthetic surface-active compounds are suitable anionic
surfactants. Suitable soaps are the alkali metal salts, alkaline
earth metal salts or unsubstituted or substituted ammonium salts of
higher fatty acids (C.sub.10-C.sub.22), e.g. the sodium or
potassium salts of oleic or stearic acid, or of naturally fatty
acid mixtures which can be obtained e.g. from coconut oil or tallow
oil. Mention may also be made of fatty acid methyltaurine salts.
More frequently, however, so-called synthetic surfactants are used,
especially fatty alcohol sulfonates, fatty alcohol sulfates,
sulfonated benzimidazole derivatives or alkylarylsulfonates. The
fatty alcohol sulfonates or sulfates are usually in the form of
alkali metal salts, alkaline earth metal salts or unsubstituted or
substituted ammonium salts and contain a C.sub.8-C.sub.22alkyl
radical, which also includes the alkyl moiety of acyl radicals,
e.g. the sodium or calcium salt of lignosulfonic acid, of dodecyl
sulfate or a mixture of fatty alcohol sulfates obtained from
natural fatty acids. These compounds also include the salts of
sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The
sulfonated benzimidazole derivatives preferably contain 2 sulfonic
acid groups and one fatty acid radical containing 8 to 22 carbon
atoms. Examples of alkylarylsulfonates are the sodium, calcium or
triethanolamine salts of dodecylbenzenesulfonic acid,
dibutylnaphthalenesulfonic acid, or of a condensate of
naphthalene-sulfonic acid and formaldehyde. Also suitable are
corresponding phosphates, e.g. salts of the phosphoric acid ester
of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide,
or phospholipids. Non-ionic surfactants are preferably polyglycol
ether derivatives of aliphatic or cycloaliphatic alcohols,
saturated or unsaturated fatty acids and alkylphenols, said
derivatives containing 3 to 30 glycol ether groups and 8 to 20
carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18
carbon atoms in the alkyl moiety of the alkylphenols. Further
suitable non-ionic surfactants are the water-soluble adducts of
polyethylene oxide with polypropylene glycol,
ethylenediaminopolypropylene glycol and alkylpolypropylene glycol
containing 1 to 10 carbon atoms in the alkyl chain, which adducts
contain 20 to 250 ethylene glycol ether groups and 10 to 100
propylene glycol ether groups. These compounds usually contain 1 to
5 ethylene glycol units per propylene glycol unit. Examples of
non-ionic surfactants are nonylphenol polyethoxyethanols, castor
oil polyglycol ethers, polypropylene/polyethylene oxide adducts,
tributylphenoxypolyethoxyethano- l, polyethylene glycol and
octylphenoxypolyethoxyethanol. Fatty acids esters of
polyoxyethylenesorbitan, e.g. polyoxyethylene sorbitan trioleate,
are also suitable. Cationic surfactants are preferably quaternary
ammonium salts which contain, as N-substituent, at least one
C.sub.8-C.sub.22alkyl radical and, as further substituents,
unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower
alkyl radicals. The salts are preferably in the form of halides,
methyl sulfates or ethyl sulfates, e.g. stearyltrimethylammonium
chloride or benzyldi(2-chloroethyl)ethylammonium bromide. The
surfactants customarily employed in formulation technology, which
can also be used in the compositions according to the invention,
are described inter alia in "Mc Cutcheon's Detergents and
Emulsifiers Annual" MC Publishing Corp., Ridgewood N.J., 1981,
Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag,
Munich/Vienna, 1981 and M. and J. Ash, "Encyclopedia of
Surfactants", Vol I-III, Chemical Publishing Co., New York,
1980-81.
[0092] The herbicidal formulations usually contain 0.1 to 99% by
weight, especially 0.1 to 95% by weight, of an active ingredient
mixture of the compound of formula I with the compounds of formula
II, III, IV, V, VI, VII, VIII, IX or X, 1 to 99.9% by weight of a
solid or liquid adjuvant, and 0 to 25% by weight, especially 0.1 to
25% by weight, of a surfactant. Whereas commercial products are
preferably formulated as concentrates, the end user will normally
employ dilute formulations. The compositions may also comprise
further ingredients, such as stabilisers, for example vegetable
oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil
or soybean oil), antifoams, for example silicone oil,
preservatives, viscosity regulators, binders, tackifiers, as well
as fertilisers or other active ingredients.
[0093] Preferred formulations are composed in particular of the
following constituents (throughout, percentages are by weight):
7 Dusts: active ingredient mixture: 0.1 to 10%, preferably 0.1 to
5% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension
concentrates: active ingredient mixture: 5 to 75%, preferably 10 to
50% water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%,
preferably 2 to 30% Wettable powders: active ingredient mixture:
0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably
1 to 15% solid carrier: 5 to 95%, preferably 15 to 90% Granules:
active ingredient mixture: 0.1 to 30%, preferably 0.1 to 15% solid
carrier: 99.5 to 70%, preferably 97 to 85%
[0094] The following Examples illustrate the invention in more
detail without limiting it.
8 Formulation Examples for mixtures of compounds of formulae I and
II, III, IV, V, VI, VII, VIII, IX or X (throughout, percentages are
by weight): F1. Solutions a) b) c) d) compound I + according 5% 10%
50% 90% to Tables 1-6 1-methoxy-3-(3-methoxy- -- 20% 20% --
propoxy)-propane polyethylene glycol 20% 10% -- -- mol. wt. 400
N-methyl-2-pyrrolidone -- -- 30% 10% atom. hydrocarbon mixture
C.sub.9-C.sub.12 75% 60% -- --
[0095] The solutions are suitable for use in the form of
microdrops.
9 F2. Wettable powders a) b) c) d) compound I + according 5% 25%
50% 80% to Tables 1-6 sodium lignosulfonate 4% -- 3% -- sodium
lauryl sulfate 2% 3% -- 4% sodium diisobutyl- -- 6% 5% 6%
naphthalenesulfonate octylphenol polyglycol ether -- 1% 2% -- (7-8
mol of ethylene oxide) highly dispersed silicic acid 1% 3% 5% 10%
kaolin 88% 62% 35% --
[0096] The active ingredients are thoroughly mixed with the
adjuvants and the mixture is thoroughly ground in a suitable mill,
affording wettable powders which can be diluted with water to give
suspensions of any desired concentration.
10 F3. Coated granules a) b) c) compound I + according 0.1% 5% 15%
to Tables 1-6 highly dispersed silicic acid 0.9% 2% 2% inorg.
carrier 99.0% 93% 83% ( 0.1-1 mm) e.g. CaCO.sub.3 or SiO.sub.2
[0097] The active ingredients are dissolved in methylene chloride,
the solution is sprayed onto the carrier and the solvent is
subsequently evaporated off in vacuo.
11 F4. Coated granules a) b) c) compound I + according 0.1% 5% 15%
to Tables 1-6 polyethylene glycol 1.0% 2% 3% mol. wt. 200 highly
dispersed silicic acid 0.9% 1% 2% inorg. carrier 98.0% 92% 80% (
0.1-1 mm) e.g. CaCO.sub.3 or SiO.sub.2
[0098] The finely ground active ingredients are uniformly applied,
in a mixer, to the carrier moistened with polyethylene glycol.
Non-dusty coated granules are obtained in this manner.
12 F5. Extruder granules a) b) c) d) compound I + according 0.1% 3%
5% 15% to Tables 1-6 sodium lignosulfonate 1.5% 2% 3% 4%
carboxymethylcellulose 1.4% 2% 2% 2% kaolin 97.0% 93% 90% 79%
[0099] The active ingredients are mixed and ground with the
adjuvants, and the mixture is moistened with water. The mixture is
extruded and then dried in a stream of air.
13 F6. Dusts a) b) c) compound I + according 0.1% 1% 5% toTables
1-6 talcum 39.9% 49% 35% kaolin 60.0% 50% 60%
[0100] Ready-for-use dusts are obtained by mixing the active
ingredients with the carriers and grinding the mixture in a
suitable mill.
14 F7. Suspension concentrates a) b) c) d) compound I + according
3% 10% 25% 50% to Tables 1-6 ethylene glycol 5% 5% 5% 5%
nonylphenol polyglycol ether -- 1% 2% -- (15 mol of ethylene oxide)
sodium lignosulfonate 3% 3% 4% 5% carboxymethylcellulose 1% 1% 1%
1% 37% aqueous formaldehyde 0.2% 0.2% 0.2% 0.2% solution silicone
oil emulsion 0.8% 0.8% 0.8% 0.8% water 87% 79% 62% 38%
[0101] The finely ground active ingredient is intimately mixed with
the adjuvants, giving a suspension concentrate from which
suspensions of any desired concentration can be obtained by
dilution with water.
[0102] It is often more practical to formulate the compound of
formula I and the mixing partners of formula II, III, IV, V, VI,
VII, VIII, IX or X individually and subsequently combine them in
the desired mixing ratio as a tank mix in water shortly before
application in an applicator.
BIOLOGICAL EXAMPLES
[0103] A synergistic effect exists whenever the action of the
active ingredient combination I and II, III, IV, V, VI, VII, VIII,
IX or X is greater than the sum of the actions of the active
ingredients applied individually. The herbicidal action to be
expected, We, for a given combination of two herbicides can be
calculated as follows (see COLBY, S. R. "Calculating synergistic
and antagonistic response of herbicide combinations". Weeds 15,
pages 20-22; 1967):
We=X+[Y. (100-X)/100]
[0104] wherein: X=% herbicidal action in the case of treatment with
the compound of formula I using an application rate of p kg per
hectare, in comparison with untreated control (=0%).
[0105] Y=% herbicidal action in the case of treatment with a
compound of formula II, III, IV, V, VI, VII, VIII, IX or X using an
application rate of q kg per hectare, in comparison with untreated
control.
[0106] We=expected herbicidal action (% herbicidal action in
comparison with untreated control) after treatment with the
compounds of formula I and II, III, IV, V, VI, VII, VIII, IX or X
at a rate of application of p+q kg of active ingredient per
hectare.
[0107] If the action actually observed is greater than the expected
value We, then synergy exists. The synergistic effect of the
combinations of the active ingredient of formula I with the active
ingredients of formula II, III, IV, V, VI, VII, VIII, IX or X is
demonstrated in the following Example.
EXAMPLE B1
Pre-Emergence Herbicidal Action
[0108] Monocotyledonous and dicotyledonous weeds and cultivated
plants are sown in standard soil in plastics pots. Immediately
after sowing, the test compounds are applied as an aqueous
suspension (500 l of water/ha). The rates of application depend on
the optimum concentrations determined under field conditions and
greenhouse conditions. Evaluation of the tests is made after 15 and
27 days (DAA=day after application) in % action. 100% denotes that
the plants have died, 0% denotes no phytotoxic action. The
combinations of the active ingredient of formula I with the active
ingredients of formula II, III, IV, V, VI, VII, VIII, IX or X
exhibit a synergistic action in this test. Examples of the
pre-emergence synergistic action of the compositions according to
the invention are given in the following Tables:
15TABLE B1 Pre-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
prometryn on DAA 15: comp. of expected value rate of formula I
prometryn 3.75 g/ha I + 250 according application 3.75 g/ha 250
g/ha g/ha prometryn to Colby test plant Sesbania 35 10 50 42
Xanthium 85 0 90 85
[0109]
16TABLE B2 Pre-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
prometryn on DAA 27: comp. of expected value rate of formula I
prometryn 3.75 g/ha I + 250 according application 3.75 g/ha 250
g/ha g/ha prometryn to Colby test plant Digitaria 25 10 80 33
Sesbania 25 0 35 25 Brachiaria 25 10 60 33 Abutilon 50 0 85 50
[0110]
17TABLE B3 Pre-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
norflurazon on DAA 27: expected expected comp of norflurazon
norflurazon 3.75 g/ha I + value 3.75 g/ha I + value rate of formula
1 500 250 500 g/ha according to 250 g/ha according to application
3.75 g/ha g/ha g/ha norflurazon Colby norflurazon Colby test plant
cotton 10 0 0 0 10 0 10 Abutilon 50 60 60 96 80 96 80 Sesbania 25
30 10 50 48 30 32 Xanthium 96 35 10 98 97 98 96
[0111] In addition to the synergistic herbicidal action of the
composition according to the invention on tne weeds, surprisingly
an advantageous antagonistic action on the cultivated plant cotton
was found, i.e. whereas the compound of formula I when applied at a
rate of 3.75 g/ha damages cotton by 10%, when 500 or 250 g/ha of
norflurazon are added to the compound of formula I the cotton is
protected to a very large extent (0% damage) while the herbicidal
action on the weeds is increased.
18TABLE B4 Pre-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
pendimethalin on DAA 15: expected value herbicidal action on
according rate of application/herbicide Xanthium to Colby 7.5 g/ha
compound of formula I 90 -- 3.75 g/ha compound of formula I 85 --
1000 g/ha pendimethalin 0 -- 500 g/ha pendimethalin 0 -- 250 g/ha
pendimethalin 0 -- 7.5 g/ha I + 1000 g/ha 97 90 pendimethalin 7.5
g/ha I + 500 g/ha 97 90 pendimethalin 7.5 g/ha I + 250 g/ha 95 90
pendimethalin 3.75 g/ha I + 1000 g/ha 90 85 pendimethalin 3.75 g/ha
I + 500 g/ha 95 85 pendimethalin 3.75 g/ha I + 250 g/ha 95 85
pendimethalin
[0112]
19TABLE B5 Pre-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
clomazone on DAA 15: expected value herbicidal action on according
rate of application/herbicide Xanthium to Colby 3.75 g/ha compound
of formula I 85 -- 500 g/ha clomazone 60 -- 250 g/ha clomazone 25
-- 125 g/ha clomazone 10 -- 3.75 g/ha I + 500 g/ha 95 94 clomazone
3.75 g/ha I + 250 g/ha 95 89 clomazone 3.75 g/ha I + 125 g/ha 95 87
clomazone
EXAMPLE B2
Post-Emergence Herbicidal Action
[0113] The test plants are raised in plastics pots under greenhouse
conditions as far as the 2- to 3-leaf stage. A standard soil is
used as the cultivation substrate. At the 2- to 3-leaf stage, the
herbicides are applied individually and as mixtures to the test
plants. The test compounds are applied in the form of an aqueous
suspension in 500 l of water/ha. The rates of application depend on
the optimum concentrations determined under field conditions and
greenhouse conditions. Evaluation of the tests is made after 11 and
22 days (DM=day after application) in % action. 100% denotes that
the plants have died, 0% denotes no phytotoxic action. The
combinations of the active ingredient of formula I with the active
ingredients of formula II, III, IV, V, VI, VII, VIII, IX or X
exhibit a synergistic action in this test. Examples of the
post-emergence synergistic action of the compositions according to
the invention are given in the following Tables.
20TABLE B6 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
fluometuron on DAA 11: expected value herbicidal action on
according rate of application/herbicide Cyperus to Colby 3.75 g/ha
compound of formula I 50 -- 1000 g/ha fluometuron 20 -- 500 g/ha
fluometuron 25 -- 250 g/ha fluometuron 0 -- 3.75 g/ha I + 1000 g/ha
70 60 fluometuron 3.75 g/ha I + 500 g/ha 70 63 fluometuron 3.75
g/ha I + 250 g/ha 60 50 fluometuron
[0114]
21TABLE B7 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
prometryn on DAA 22: expected value herbicidal action on according
rate of application/herbicide Soanium nigrum to Colby 7.5 g/ha
compound of formula I 15 -- 3.75 g/ha compound of formula I 0 --
1.88 g/ha compound of formula I 0 -- 1000 g/ha prometryn 20 -- 500
g/ha prometryn 0 -- 250 g/ha prometryn 0 -- 7.5 g/ha I + 1000 g/ha
35 32 prometryn 7.5 g/ha I + 500 g/ha prometryn 25 15 7.5 g/ha I +
250 g/ha prometryn 25 15 3.75 g/ha I + 1000 g/ha 50 20 prometryn
3.75 g/ha I + 500 g/ha prometryn 45 0 3.75 g/ha I + 250 g/ha
prometryn 10 0 1.88 g/ha I + 1000 g/ha 30 20 prometryn 1.88 g/ha I
+ 500 g/ha prometryn 25 0 1.88 g/ha I + 250 g/ha prometryn 25 0
[0115]
22TABLE B8 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
metolachlor on DAA 22: expected value herbicidal action on
according rate of application/herbicide Sorghum hal to Colby 1.88
g/ha compound of formula I 75 -- 1500 g/ha metolachlor 0 -- 750
g/ha metolachlor 0 -- 375 g/ha metolachlor 0 -- 1.88 g/ha I + 1500
g/ha 90 75 metolachlor 1.88 g/ha I + 750 g/ha 95 75 metolachlor
1.88 g/ha I + 375 g/ha 92 75 metolachlor
[0116]
23TABLE B9 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
.alpha.-metolachlor on Abutilon on DAA 22: expected value
herbicidal action on according rate of application/herbicide
Abutilon to Colby 1.88 g/ha compound of formula I 55 -- 500 g/ha
.alpha.-metolachlor 0 -- 250 g/ha .alpha.-metolachlor 0 -- 1.88
g/ha I + 500 g/ha 65 66 .alpha.-metolachlor 1.88 g/ha I + 250 g/ha
95 66 .alpha.-metolachlor
[0117]
24TABLE B10 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
.alpha.-metolachlor on Cassia sp. on DAA 11: expected value
herbicidal action on according rate of application/herbicide Cassa
sp. to Colby 1.88 g/ha compound of formula I 70 -- 1000 g/ha
.alpha.-metolachlor 0 -- 500 g/ha .alpha.-metolachlor 0 -- 250 g/ha
.alpha.-metolachlor 0 -- 1.88 g/ha I + 1000 g/ha 90 70
.alpha.-metolachlor 1.88 g/ha I + 500 g/ha 80 70
.alpha.-metolachlor 1.88 g/ha I + 250 g/ha 90 70
.alpha.-metolachlor
[0118]
25TABLE B11 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
.alpha.-metolachlor on Ipomoea on DAA 11: expected value herbicidal
action on according rate of application/herbicide Ipomoea to Colby
1.88 g/ha compound of formula I 80 -- 1000 g/ha .alpha.-metolachlor
0 -- 500 g/ha .alpha.-metolachlor 0 -- 250 g/ha .alpha.-metolachlor
0 -- 1.88 g/ha I + 1000 g/ha 90 80 .alpha.-metolachlor 1.88 g/ha I
+ 500 g/ha 90 80 .alpha.-metolachlor 1.88 g/ha I + 250 g/ha 85 80
.alpha.-metolachlor
[0119]
26TABLE B12 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
.alpha.-metolachlor on Sesbania on DAA 11: expected value
herbicidal action on according rate of application/herbicide
Sesbania to Colby 1.88 g/ha compound of formula I 70 -- 1000 g/ha
.alpha.-metolachlor 0 -- 500 g/ha .alpha.-metolachlor 0 -- 250 g/ha
.alpha.-metolachlor 0 -- 1.88 g/ha I + 1000 g/ha 85 70
.alpha.-metolachlor 1.88 g/ha I + 500 g/ha 80 70
.alpha.-metolachlor 1.88 g/ha I + 250 g/ha 85 70
.alpha.-metolachlor
[0120]
27TABLE B13 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
.alpha.-metolachlor on Xanthium on DAA 11: expected value
herbicidal action on according rate of application/herbicide
Xanthium to Colby 1.88 g/ha compound of formula I 85 -- 1000 g/ha
.alpha.-metolachlor 0 -- 500 g/ha .alpha.-metolachlor 0 -- 250 g/ha
.alpha.-metolachlor 0 -- 1.88 g/ha I + 1000 g/ha 95 85
.alpha.-metolachlor 1.88 g/ha I + 500 g/ha 95 85
.alpha.-metolachlor 1.88 g/ha I + 250 g/ha 95 85
.alpha.-metolachlor
[0121]
28TABLE B14 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
pyrithiobac on DAA 11: herbicidal action on expected value rate of
application/herbicide Cassia sp. according to Colby 1.88 g/ha
compound of formula I 70 -- 100 g/ha pyrithiobac 70 -- 50 g/ha
pyrithiobac 80 -- 25 g/ha pyrithiobac 50 -- 1.88 g/ha I + 100 g/ha
95 91 pyrithiobac 1.88 g/ha I + 50 g/ha 95 94 pyrithiobac 1.88 g/ha
I + 25 g/ha 95 85 pyrithiobac
[0122]
29TABLE B15 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
MSMA on Cassia sp. on DAA 11: herbicidal rate of action on expected
value application/herbicide Cassia sp. according to Colby 1.88 g/ha
compound of formula I 70 -- 2000 g/ha MSMA 50 -- 1000 g/ha MSMA 20
-- 500 g/ha MSMA 0 -- 1.88 g/ha I + 2000 g/ha MSMA 85 85 1.88 g/ha
I + 1000 g/ha MSMA 95 76 1.88 g/ha I + 500 g/ha MSMA 95 70
[0123]
30TABLE B16 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
MSMA on Sesbania on DAA 11: herbicidal action on expected value
rate of application/herbicide Sesbania according to Colby 1.88 g/ha
compound of formula I 70 -- 2000 g/ha MSMA 20 -- 1000 g/ha MSMA 0
-- 500 g/ha MSMA 0 -- 1.88 g/ha I + 2000 g/ha MSMA 90 76 1.88 g/ha
I + 1000 g/ha MSMA 90 70 1.88 g/ha I + 500 g/ha MSMA 90 70
[0124]
31TABLE B17 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
bromoxynil on Solanum on DAA 11: herbicidal action on expected
value rate of application/herbicide Solanum according to Colby 7.5
g/ha compound of formula I 20 -- 1000 g/ha bromoxynil 40 -- 500
g/ha bromoxynil 35 -- 7.5 g/ha I .div. 1000 g/ha 80 52 bromoxynil
7.5 g/ha I + 500 g/ha bromoxynil 50 48
[0125]
32TABLE B18 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
glyphosate on DAA 11: comp. of 1.88 g/ha I + expected value rate of
formula I glyphosate 187 g/ha according application 1.88 g/ha 187
g/ha glyphosate to Colby test plant Abutilon 75 30 90 83 Cassia 70
40 90 82 Digitaria 25 85 95 89 Ipomoea 80 30 90 86 Sesbania 70 60
90 88 Sorghum 70 40 85 82
[0126]
33TABLE B19 Post-emergence herbicidal action of the composition
according to the invention comprising the compound of formula I and
glufosinate on DAA 22: comp. of 1.88 g/ha I + expected value rate
of formula I glufosinate 250 g/ha according application 1.88 g/ha
250 g/ha glufosinate to Colby test plant Abutilon 55 55 90 80
Cyperus 70 35 85 81 Digitaria 15 75 97 79 Sorghum 75 85 98 96
* * * * *