U.S. patent application number 10/443628 was filed with the patent office on 2003-12-04 for selective herbicidal composition.
Invention is credited to Glock, Jutta, Hudetz, Manfred.
Application Number | 20030224937 10/443628 |
Document ID | / |
Family ID | 25688580 |
Filed Date | 2003-12-04 |
United States Patent
Application |
20030224937 |
Kind Code |
A1 |
Glock, Jutta ; et
al. |
December 4, 2003 |
Selective herbicidal composition
Abstract
A mixture of a herbicidally effective amount of a haloacetamide
of formula I 1 wherein R.sub.0 is methyl or ethyl, and to
antagonise the herbicide, an antidotally effective amount of a
compound of formula II as safener R--CHYCl (I) wherein R is a
radical of formula 2 or R is a radical of formula or R is a radical
of formula 3 or R is a radical of formula 4 or R is a radical of
formula 5 or R is a radical of formula
(H.sub.5C.sub.2O).sub.2P(O)CH.sub.2NHCO-- or 6 (P--X).sub.n
R.sub.25 or R is a radical of formula 7 or of formula 8 in each of
which formulae the substituents are as defined in claim 1 and Y is
chloro, or Y is hydrogen if R is a radical of formula
(H.sub.5C.sub.2O).sub.2P(O)CH.sub.2NHCO--, are very suitable for
controlling weeds in crops of cultivated plants, in particular
maize.
Inventors: |
Glock, Jutta; (Mumpf,
CH) ; Hudetz, Manfred; (Rheinfelden, CH) |
Correspondence
Address: |
SYNGENTA CROP PROTECTION , INC.
PATENT AND TRADEMARK DEPARTMENT
410 SWING ROAD
GREENSBORO
NC
27409
US
|
Family ID: |
25688580 |
Appl. No.: |
10/443628 |
Filed: |
May 22, 2003 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10443628 |
May 22, 2003 |
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08819014 |
Mar 17, 1997 |
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6569806 |
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Current U.S.
Class: |
504/105 ;
504/111 |
Current CPC
Class: |
A01N 37/22 20130101;
A01N 37/22 20130101; A01N 43/84 20130101; A01N 25/32 20130101; A01N
37/22 20130101; A01N 2300/00 20130101 |
Class at
Publication: |
504/105 ;
504/111 |
International
Class: |
A01N 025/32 |
Foreign Application Data
Date |
Code |
Application Number |
Jun 3, 1994 |
CH |
1758/94-0 |
Jul 14, 1994 |
CH |
2253/94-8 |
Claims
What is claimed is:
1. A composition for the selective control of weeds in crops of
cultivated plants, comprising, in addition to inert carriers and
adjuvants, as active component, a mixture of a) a herbicidally
effective amount of a compound of formula I 47wherein R.sub.0 is
methyl or ethyl, and b) to antagonise the herbicide, an antidotally
effective amount of a compound of formula II as safener R--CHYCl
(II) wherein R is a radical of formula 48wherein R.sub.33 and
R.sub.34 are each independently of the other C.sub.1-C.sub.6alkyl
or C.sub.2-C.sub.6alkenyl; or R.sub.33 and R.sub.34, taken
together, are 49R.sub.35 and R.sub.36 are each independently of the
other hydrogen or C.sub.1-C.sub.6alkyl; or R.sub.33 and R.sub.34,
taken together, are 50R.sub.37 and R.sub.38 are each independently
of the other C.sub.1-C.sub.4alkyl, or R.sub.37 and R.sub.38, taken
together, are --(CH.sub.2).sub.5--; --R.sub.39 is hydrogen,
C.sub.1-C.sub.4alkyl or 51or R.sub.33 and R.sub.34, taken together,
are 52or 53and R.sub.40, R.sub.41, R.sub.42, R.sub.43, R.sub.44,
R.sub.45, R.sub.46, R.sub.47, R.sub.48, R.sub.49, R.sub.50,
R.sub.51, R.sub.52, R.sub.53, R.sub.54 and R.sub.55 are each
independently of one another hydrogen or C.sub.1-C.sub.4alkyl, or R
is a radical of formula 54or 55or R is a radical of formula
56wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each
independently of one another hydrogen, C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkoxy or C.sub.1-C.sub.4haloalkyl, R.sub.5,
R.sub.6, R.sub.7 and R.sub.8 are each independently of one another
hydrogen, C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4haloalkyl, or R is
a radical of formula 57wherein R.sub.9 is C.sub.1-C.sub.4alkyl or
halogen, R.sub.10 is halogen, R.sub.11 and R.sub.12 are each
independently of the other hydrogen or C.sub.1-C.sub.4alkyl, and Q
is C.sub.1-C.sub.4alkylene or alkyl-substituted
C.sub.1-C.sub.4alkylene, or R is a radical of formula 58wherein
R.sub.14 is hydrogen, halogen, C.sub.1-C.sub.4alkyl,
dioxymethylene, C.sub.1-C.sub.4alkoxy, C.sub.2-C.sub.4alkenyloxy,
C.sub.2-C.sub.4alkynyloxy or cyano-C.sub.1-C.sub.4alkyl, P is
C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl,
C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.8cycloalkyl,
C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenoxy-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkynoxy-C.s- ub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenylthio-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkynylth- io-C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl- ,
C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl,
halo-C.sub.1-C.sub.4alkyl, cyano-C.sub.1-C.sub.4alkyl,
2,2-di-C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-2-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-4-yl-C.sub.1-C.sub.4- alkyl,
2,2-di-C.sub.1-C.sub.4alkyl-1,3-dioxolan-4-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxan-2-yl-C.sub.1-C.sub.4alkyl,
2-benzopyranyl-C.sub.1-C.sub.4alkyl- ,
C.sub.1-C.sub.4alkoxycarbonyl or C.sub.2-C.sub.4alkenyloxycarbonyl
or tetrahydrofurfuryl-C.sub.1-C.sub.4alkyl, the group P--X is also
halo-C.sub.1-C.sub.4alkyl, X is O, S, SO or SO.sub.2, n is 1, 2 or
3, A is a C.sub.1-C.sub.8hydrocarbon radical or a
C.sub.1-C.sub.8hydrocarbon radical which is substituted by alkoxy,
alkylthio, fluoro, cyano or haloalkyl, and R.sub.13 is hydrogen, a
C.sub.1-C.sub.5hydrocarbon radical or a C.sub.1-C.sub.5hydrocarbon
radical which is substituted by alkoxy, polyalkoxy, halogen, cyano
or trifluoromethyl; C.sub.3-C.sub.8cycloalkyl,
C.sub.1-C.sub.4alkyl-C.sub.3-C.sub.8cycloalkyl,
di-C.sub.1-C.sub.4alkoxy-- C.sub.1-C.sub.4alkyl,
1,3-dioxolan-2-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-4-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxan-2-yl-C.sub.1-C.sub.4al- kyl, furyl-C.sub.1-C.sub.4alkyl,
tetrahydrofuryl-C.sub.1-C.sub.4alkyl, or a radical of formula
--NHCO.sub.2R.sub.01, --CH.sub.2CO.sub.2R.sub.01,
--CH(CH.sub.3)CO.sub.2R.sub.01, or
--CH(R.sub.02)--C(R.sub.03).dbd.NOR.su- b.04, wherein R.sub.01 is
methyl, ethyl, propyl, isopropyl or allyl, R.sub.02 and R.sub.03
are each hydrogen or C.sub.1-C.sub.4alkyl, and R.sub.04 is
hydrogen, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl or
C.sub.2-C.sub.4alkynyl, or R is a radical of formula
(H.sub.5C.sub.2O).sub.2P(O)CH.sub.2NHCO-- or 59R15
R.sup.5P(O)CR1.sub.7R.sub.8N(NR.sub.19R.sub.20)co
7P(.degree.)CR17R18N(NR- 19R20)C.degree.wherein R.sub.15 and
R.sub.16 are each independently of the other hydroxyl,
C.sub.1-C.sub.4alkyl, aryl, C.sub.1-C.sub.4alkoxy,
C.sub.2-C.sub.4alkenyloxy, C.sub.2-C.sub.4alkynyloxy,
C.sub.2-C.sub.4haloalkoxy, C.sub.2-C.sub.8alkoxyalkoxy,
C.sub.1-C.sub.4cyanoalkoxy, C.sub.1-C.sub.4phenylalkoxy or aryloxy
or aryloxy which is substituted by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, R.sub.17 is hydrogen, C.sub.1-C.sub.4alkyl
or phenyl, or phenyl which is substituted by halogen, cyano, nitro
or C.sub.1-C.sub.4alkoxy, R.sub.18 is hydrogen, or
C.sub.1-C.sub.4alkyl, R.sub.19 is hydrogen or a radical of formula
--COCX.sub.1X.sub.2--R.sub.0- 6, or an alkenoyl radical which
contains 2 to 4 carbon atoms in the alkenyl moiety and which is
substituted by halogen, and X.sub.1 and X.sub.2 are each
independently of the other hydrogen or halogen, or is a radical of
formula --COOR.sub.07 or --COR.sub.08 or a C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl or C.sub.1-C.sub.4phenylalky- l radical
which may be substituted at the phenyl ring by halogen, cyano,
nitro or C.sub.1-C.sub.4alkoxy, and R.sub.20 is hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl or
C.sub.2-C.sub.4alkynyl, R.sub.06 is hydrogen, halogen or
C.sub.1-C.sub.6alkyl, R.sub.07 is C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4phenylalkyl or C.sub.1-C.sub.4phenylalkyl which is
substituted in the phenyl moiety by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, and R.sub.08 is C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, phenyl,
C.sub.1-C.sub.4phenylalkyl or C.sub.1-C.sub.4phenylalkyl which is
substituted in the phenyl moiety by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, or R is a radical of formula 60or of formula
61wherein R.sub.21 is methyl, ethyl, propyl, 1-methylethyl,
2-propenyl, 2-butenyl, 1,1-dimethyl-2-propenyl, 2-propynyl or
2-methyl-2-propynyl, and R.sub.22, R.sub.23, R.sub.24 and R.sub.25
are each independently of one another hydrogen or methyl, and Y is
chloro, or Y is hydrogen if R is a radical of formula
(H.sub.5C.sub.2O).sub.2P(O)CH.sub.2NHCO--.
2. A composition according to claim 1, wherein R is a radical of
formula 62wherein R.sub.33 and R.sub.34 together are 63R.sub.37 and
R.sub.38 are each independently of the other C.sub.1-C.sub.4alkyl;
or R.sub.37 and R.sub.38, taken together, are --(CH.sub.2).sub.5--;
and R.sub.39 is hydrogen, C.sub.1-C.sub.4alkyl or 64
3. A composition according to claim 1, wherein R is a radical of
formula 65wherein R.sub.21 is methyl, ethyl, propyl, 2-propenyl or
2-butenyl, and R.sub.22 and R.sub.25 are hydrogen.
4. A composition according to claim 3, wherein R.sub.21 is
2-propenyl.
5. A composition according to claim 1, wherein R is a radical of
formula 66wherein R.sub.1 to R.sub.8 are each independently of one
another hydrogen or C.sub.1-C.sub.4alkyl.
6. A composition according to claim 5, wherein R.sub.1 to R.sub.7
are hydrogen and R.sub.8 is methyl.
7. A composition according to claim 1, wherein R is a radical of
formula 67wherein R.sub.14 is hydrogen, C.sub.1-C.sub.4alkyl or
C.sub.1-C.sub.4alkoxy, P is C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl or C.sub.2-C.sub.4alkynyl, X is O or S, n is
1, A is a C.sub.1-C.sub.8hydrocarbon radical and R.sub.13 is
hydrogen or a C.sub.1-C.sub.5hydrocarbon radical.
8. A composition according to claim 7, wherein R.sub.14 is
C.sub.1-C.sub.4alkoxy, P is C.sub.1-C.sub.4alkyl, X is O, A is
C.sub.1-C.sub.4alkylene and R.sub.13 is C.sub.1-C.sub.4alkyl.
9. A composition according to claim 8, wherein R.sub.14 is methoxy,
P is methyl, A is methylene and R.sub.13 is isopropyl.
10. A composition according to claim 1, wherein R is a radical of
formula 68wherein R.sub.15 and R.sub.16 are each independently of
the other hydroxyl, C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4alkoxy,
R.sub.17 and R.sub.18 are each independently of the other hydrogen
or C.sub.1-C.sub.4alkyl, and R.sub.19 is hydrogen or a radical of
formula --COOR.sub.07, wherein R.sub.07 is C.sub.1-C.sub.4alkyl,
and R.sub.20 is hydrogen or C.sub.1-C.sub.4alkyl.
11. A composition according to claim 10, wherein R.sub.16 and
R.sub.15 are C.sub.1-C.sub.4alkoxy, R.sub.17 and R.sub.18 are
hydrogen, R.sub.19 is a radical of formula --COOR.sub.07, wherein
R.sub.07 is C.sub.1-C.sub.4alkyl, and R.sub.20 is hydrogen.
12. A composition according to claim 11, wherein R.sub.15 and
R.sub.16 are isopropoxy and R.sub.19 is --COOC.sub.2H.sub.5.
13. A composition according to claim 1, which contains, as compound
of formula II, a compound of formula III 69or of formula IV 70or of
formula V 71
14. A method of selectively controlling weeds and grasses in crops
of cultivated plants, which comprises treating said plants, the
seeds or the locus thereof, concurrently or separately, with an
effective amount of a herbicide of formula I according to claim 1
and, to antagonise said herbicide, an antidotally effective amount
of a compound of formula II according to claim 1.
15. A method according to claim 14, which comprises treating crops
of cultivated plants or areas intended for cropping with cultivated
plants, with 0.001 to 10 kg/ha of a compound of formula I and an
amount of 0.005 to 0.5 kg/ha of a compound of formula II.
16. A method according to claim 14 of selectively controlling weeds
and grasses in crops of maize.
Description
[0001] The present invention relates to a selective herbicidal
composition for controlling grasses and weeds in crops of
cultivated plants, especially in crops of maize, which composition
comprises a herbicide and a safener (antidote) and protects the
cultivated plants, but not the weeds, from the phytotoxic action of
the herbicide, and to the use of said composition, or of the
combination of herbicide and safener, for controlling weeds in
crops of cultivated plants.
[0002] When applying herbicides, the cultivated plants may also
suffer severe damage owing to factors that include the
concentration of the herbicide and the mode of application, the
cultivated plant itself, the nature of the soil, and the climatic
conditions such as exposure to light, temperature and rainfall.
[0003] To counteract this problem and similar ones, the proposal
has already been made to use different compounds as safeners which
are able to antagonise the harmful action of the herbicide on the
cultivated plant, i.e. to protect the cultivated plant while
leaving the herbicidal action on the weeds to be controlled
virtually unimpaired. It has, however, been found that the proposed
safeners often have a very species-specific action, not only with
respect to the cultivated plants but also to the herbicide, and in
some cases also subject to the mode of application, i.e. a specific
safener will often be suitable only for a specific cultivated plant
and a specific class of herbicide.
[0004] It has now been found that certain chloro- and
dichloroacetamides are suitable for protecting cultivated plants
from the phytotoxic action of the compound
aRS,1'S(-)N-(1'-methyl-2'-methoxyethyl)-N-chloracetyl-2-e-
thyl-6-methylaniline of formula I 9
[0005] wherein R.sub.0 is methyl or ethyl.
[0006] Accordingly, the invention provides a selective herbicidal
composition comprising, in addition to conventional inert
formulation assistants such as carriers, solvents and wetting
agents, as active component, a mixture of
[0007] a) a herbicidally effective amount of a compound of formula
I 10
[0008] wherein R.sub.0 is methyl or ethyl, and
[0009] b) to antagonise the herbicide, an antidotally effective
amount of a compound of formula II as safener
R--CHYCl (II)
[0010] wherein R is a radical of formula 11
[0011] wherein
[0012] R.sub.33 and R.sub.34 are each independently of the other
C.sub.1-C.sub.6alkyl or C.sub.2-C.sub.6alkenyl; or R.sub.33 and
R.sub.34, taken together, are 12
[0013] R.sub.35 and R.sub.36 are each independently of the other
hydrogen or C.sub.1-C.sub.6alkyl; or R.sub.33 and R.sub.34, taken
together, are 13
[0014] R.sub.37 and R.sub.38 are each independently of the other
C.sub.1-C.sub.4alkyl, or R.sub.37 and R.sub.38, taken together, are
--(CH.sub.2).sub.5--;
[0015] R.sub.39 is hydrogen, C.sub.1-C.sub.4alkyl or 14
[0016] or R.sub.33 and R.sub.34, taken together, are 15
[0017] or 16
[0018] and R.sub.40, R.sub.41, R.sub.42, R.sub.43, R.sub.44,
R.sub.45, R.sub.46, R.sub.47, R.sub.48, R.sub.49, R.sub.50,
R.sub.51, R.sub.52, R.sub.53, R.sub.54 and R.sub.55 are each
independently of one another hydrogen or C.sub.1-C.sub.4alkyl, or R
is a radical of formula 17
[0019] or 18
[0020] or R is a radical of formula 19
[0021] wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each
independently of one another hydrogen, C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkoxy or C.sub.1-C.sub.4haloalkyl, R.sub.5,
R.sub.6, R.sub.7 and R.sub.8 are each independently of one another
hydrogen, C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4haloalkyl, or R is
a radical of formula 20
[0022] wherein R.sub.9 is C.sub.1-C.sub.4alkyl or halogen, R.sub.10
is halogen, R.sub.11 and R.sub.12 are each independently of the
other hydrogen or C.sub.1-C.sub.4alkyl, and Q is
C.sub.1-C.sub.4alkylene or alkyl-substituted
C.sub.1-C.sub.4alkylene,
[0023] or R is a radical of formula 21
[0024] wherein R.sub.14 is hydrogen, halogen, C.sub.1-C.sub.4alkyl,
dioxymethylene, C.sub.1-C.sub.4alkoxy, C.sub.2-C.sub.4alkenyloxy,
C.sub.2-C.sub.4alkynyloxy or cyano-C.sub.1-C.sub.4alkyl, P is
C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl,
C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.8cycloalkyl,
C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenoxy-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkynoxy-C.s- ub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkylthio-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenylthio-C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkynylth- io-C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4alkylsulfinyl-C.sub.1-C.sub.4alkyl- ,
C.sub.1-C.sub.4alkylsulfonyl-C.sub.1-C.sub.4alkyl,
halo-C.sub.1-C.sub.4alkyl, cyano-C.sub.1-C.sub.4alkyl,
2,2-di-C.sub.1-C.sub.4alkoxy-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-2-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-4-yl-C.sub.1-C.sub.4- alkyl,
2,2-di-C.sub.1-C.sub.4alkyl-1,3-dioxolan-4-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxan-2-yl-C.sub.1-C.sub.4alkyl,
2-benzopyranyl-C.sub.1-C.sub.4alkyl- ,
C.sub.1-C.sub.4alkoxycarbonyl or C.sub.2-C.sub.4alkenyloxycarbonyl
or tetrahydrofurfuryl-C.sub.1-C.sub.4alkyl, the group P--X is also
halo-C.sub.1-C.sub.4alkyl, X is O, S, SO or SO.sub.2, n is 1, 2 or
3, A is a C.sub.1-C.sub.8hydrocarbon radical or a
C.sub.1-C.sub.8hydrocarbon radical which is substituted by alkoxy,
alkylthio, fluoro, cyano or haloalkyl, and R.sub.13 is hydrogen, a
C.sub.1-C.sub.5hydrocarbon radical or a C.sub.1-C.sub.5hydrocarbon
radical which is substituted by alkoxy, polyalkoxy, halogen, cyano
or trifluoromethyl; C.sub.3-C.sub.8cycloalkyl,
C.sub.1-C.sub.4alkyl-C.sub.3-C.sub.8cycloalkyl,
di-C.sub.1-C.sub.4alkoxy-- C.sub.1-C.sub.4alkyl,
1,3-dioxolan-2-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxolan-4-yl-C.sub.1-C.sub.4alkyl,
1,3-dioxan-2-yl-C.sub.1-C.sub.4al- kyl, furyl-C.sub.1-C.sub.4alkyl,
tetrahydrofuryl-C.sub.1-C.sub.4alkyl, or a radical of formula
--NHCO.sub.2R.sub.01, --CH.sub.2CO.sub.2R.sub.01,
--CH(CH.sub.3)CO.sub.2R.sub.01 or
--CH(R.sub.02)--C(R.sub.03).dbd.NOR.sub- .04, wherein R.sub.01 is
methyl, ethyl, propyl, isopropyl or allyl, R.sub.02 and R.sub.03
are each hydrogen or C.sub.1-C.sub.4alkyl, and R.sub.04 is
hydrogen, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl or
C.sub.2-C.sub.4alkynyl, or R is a radical of formula
(H.sub.5C.sub.2O).sub.2P(O)CH.sub.2NHCO-- or 22
[0025] wherein R.sub.15 and R.sub.16 are each independently of the
other hydroxyl, C.sub.1-C.sub.4alkyl, aryl, C.sub.1-C.sub.4alkoxy,
C.sub.2-C.sub.4alkenyloxy, C.sub.2-C.sub.4alkynyloxy,
C.sub.2-C.sub.4haloalkoxy, C.sub.2-C.sub.8alkoxyalkoxy,
C.sub.1-C.sub.4cyanoalkoxy, C.sub.1-C.sub.4phenylalkoxy or aryloxy
or aryloxy which is substituted by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, R.sub.17 is hydrogen, C.sub.1-C.sub.4alkyl
or phenyl, or phenyl which is substituted by halogen, cyano, nitro
or C.sub.1-C.sub.4alkoxy, R.sub.18 is hydrogen, or
C.sub.1-C.sub.4alkyl, R.sub.19 is hydrogen or a radical of formula
--COCX.sub.1X.sub.2--R.sub.0- 6, or an alkenoyl radical which
contains 2 to 4 carbon atoms in the alkenyl moiety and which is
substituted by halogen, and X.sub.1 and X.sub.2 are each
independently of the other hydrogen or halogen, or is a radical of
formula --COOR.sub.07 or --COR.sub.08 or a C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl or C.sub.1-C.sub.4phenylalky- l radical
which may be substituted at the phenyl ring by halogen, cyano,
nitro or C.sub.1-C.sub.4alkoxy, and R.sub.20 is hydrogen,
C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl or
C.sub.2-C.sub.4alkynyl, R.sub.06 is hydrogen, halogen or
C.sub.1-C.sub.6alkyl, R.sub.07 is C.sub.1-C.sub.4alkyl,
C.sub.1-C.sub.4phenylalkyl or C.sub.1-C.sub.4phenylalkyl which is
substituted in the phenyl moiety by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, and R.sub.8 is C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, phenyl,
C.sub.1-C.sub.4phenylalkyl or C.sub.1-C.sub.4phenylalkyl which is
substituted in the phenyl moiety by halogen, cyano, nitro or
C.sub.1-C.sub.4alkoxy, or R is a radical of formula 23
[0026] or of formula 24
[0027] wherein R.sub.21 is methyl, ethyl, propyl, 1-methylethyl,
2-propenyl, 2-butenyl, 1,1-dimethyl-2-propenyl, 2-propynyl or
2-methyl-2-propynyl, and R.sub.22, R.sub.23, R.sub.24 and R.sub.25
are each independently of one another hydrogen or methyl,
[0028] and Y is chloro, or
[0029] Y is hydrogen if R is a radical of formula
(H.sub.5C.sub.2O).sub.2P- (O)CH.sub.2NHCO--.
[0030] The alkyl groups cited in connection with the compounds of
formula II may be straight-chain or branched and are typically
methyl, ethyl, propyl, butyl, pentyl and hexyl, as well as branched
isomers thereof. Suitable alkenyl radicals are derived from the
aforementioned alkyl radicals. Aryloxy is most suitably phenyl and
naphthoxy. Hydrocarbon radicals will be understood as meaning
monovalent or divalent, saturated or unsaturated straight-chain or
branched, or saturated or unsaturated cyclic radicals of carbon and
hydrogen, typically alkyl, cycloalkyl, alkenyl, alkynyl,
cycloalkenyl and phenyl.
[0031] The invention further relates to the use of the novel
composition for controlling weeds and grasses in crops of
cultivated plants, in particular maize.
[0032] Preferred compounds of formula II for use in the novel
composition are those wherein R is a radical of formula 25
[0033] wherein R.sub.33 and R.sub.34 together are 26
[0034] R.sub.37 and R.sub.38 are each independently of the other
C.sub.1-C.sub.4alkyl; or R.sub.37 and R.sub.38, taken together, are
--(CH.sub.2).sub.5--; and R.sub.39 is hydrogen,
C.sub.1-C.sub.4alkyl or 27
[0035] Examples of particularly suitable compounds of formula II
are listed in the following Tables 1 and 2.
1TABLE 1 Compounds of formula II (II) 28 Cmpd. No. R.sub.33
R.sub.34 R.sub.33 + R.sub.34 1.001 CH.sub.2.dbd.CHCH.sub.2
CH.sub.2.dbd.CHCH.sub.2 -- 1.002 -- -- 29 1.003 -- -- 30 1.004 --
-- 31 1.005 -- -- 32 1.006 -- -- 33 1.007 -- -- 34 1.008 -- -- 35
1.009 -- -- 36 1.010 37 CH.sub.2.dbd.CHCH.sub.2 -- 1.011 38
(CH.sub.3).sub.2CH-- --
[0036]
2TABLE 2 Compounds of formula II 2.1
C.sub.2H.sub.5O).sub.2P(O)--CH.sub.2--NHCO--CH.sub.2Cl 2.2 39
[0037] Another group of preferred compounds of formula I comprises
those compounds wherein R is a radical of formula 40
[0038] wherein R.sub.21 is methyl, ethyl, propyl, 2-propenyl or
2-butenyl, and R.sub.22 and R.sub.25 are hydrogen. Among this group
of compounds, that compound is particularly preferred wherein
R.sub.21 is 2-propenyl.
[0039] Further preferred compounds of formula II are those wherein
R is a radical of formula 41
[0040] wherein R.sub.1 to R.sub.8 are each independently of one
another hydrogen or C.sub.1-C.sub.4alkyl. Those compounds are
particularly suitable wherein R.sub.1 to R.sub.7 are hydrogen and
R.sub.8 is methyl.
[0041] In another group of particularly suitable compounds R is a
radical of formula 42
[0042] wherein R.sub.14 is hydrogen, C.sub.1-C.sub.4alkyl or
C.sub.1-C.sub.4alkoxy, P is C.sub.1-C.sub.4alkyl,
C.sub.2-C.sub.4alkenyl or C.sub.2-C.sub.4alkynyl, X is O or S, n is
1, A is a C.sub.1-C.sub.8hydrocarbon radical and R.sub.13 is
hydrogen or a C.sub.1-C.sub.5hydrocarbon radical. Among this group
of compounds, those compounds of formula II are particularly
suitable wherein R.sub.14 is C.sub.1-C.sub.4alkoxy, P is
C.sub.1-C.sub.4alkyl, X is 0, A is C.sub.1-C.sub.4alkylene and
R.sub.13 is C.sub.1-C.sub.4alkyl. The compound in which R.sub.14 is
methoxy, P is methyl, A is methylene and R.sub.13 is isopropyl is
of particular interest.
[0043] A further group of preferred compounds of formula II is that
wherein R is a radical of formula 43
[0044] wherein R.sub.15 and R.sub.16 are each independently of the
other hydroxyl, C.sub.1-C.sub.4alkyl or C.sub.1-C.sub.4alkoxy,
R.sub.17 and R.sub.18 are each independently of the other hydrogen
or C.sub.1-C.sub.4alkyl, and R.sub.19 is hydrogen or a radical of
formula --COOR.sub.07, wherein R.sub.07 is C.sub.1-C.sub.4alkyl,
and R.sub.20 is hydrogen or C.sub.1-C.sub.4alkyl. Most preferably
R.sub.16 and R.sub.15 are C.sub.1-C.sub.4alkoxy, R.sub.17 and
R.sub.18 are hydrogen, R.sub.19 is a radical of formula
--COOR.sub.07, wherein R.sub.07 is C.sub.1-C.sub.4alkyl, and
R.sub.20 is hydrogen. The compound wherein R.sub.15 and R.sub.16
are isopropoxy and R.sub.19 is --COOC.sub.2H.sub.5 is of particular
importance.
[0045] Particularly suitable compositions contain, as compound of
formula II, a compound of formula III 44
[0046] or of formula IV 45
[0047] or of formula V 46
[0048] The compound of formula I used in the practice of this
invention and the preparation thereof is described, inter alia, in
U.S. Pat. No. 5,002,606. The compounds of formula II used in the
novel compositions and the preparation thereof are disclosed inter
alia, in U.S. Pat. No. 4,971,618, U.S. Pat. No. 3,959,304, U.S.
Pat. No. 4,256,481, U.S. Pat. No. 4,708,735, EP-A-149 974, EP-A-304
409, EP-A-31 686, EP-A-54 278, EP-A-23 305, U.S. Pat. No.
4,846,880, EP-A-143 078, EP-A-163 607, EP-A-126 710, as well as in
DE-A-2 948 535.
[0049] The invention also relates to a method of selectively
controlling weeds in crops of cultivated plants, which comprises
treating said cultivated plants, the seeds or seedlings or the crop
area thereof, concurrently or separately, with a herbicidally
effective amount of the compound of formula I and, to antagonise
the herbicide, an antidotally effective amount of a compound of
formula II.
[0050] Suitable cultivated plants which can be protected by the
compounds of formula II against the harmful action of the
aforementioned herbicide are preferably those important in the food
or textile sector, typically sugar cane and, in particular, millet
and maize, as well as rice and other varieties of cereals such as
wheat, rye, barley and oats.
[0051] The weeds to be controlled may be monocot as well as dicot
weeds.
[0052] Crop areas are the areas already under cultivation with the
crop plants or seeds thereof, as well as the areas intended for
cultivation with said crop plants.
[0053] Depending on the end use, a safener of formula TI can be
used for pretreating seeds of the crop plants (dressing of seeds or
seedlings) or it can be incorporated in the soil before or after
sowing. It can, however, also be applied by itself alone or
together with the herbicide pre- or postemergence. Treatment of the
plant or the seeds with the safener can therefore in principle be
carried out irrespective of the time of application of the
phytotoxic chemical. Treatment of the plant can, however, also be
carried out by simultaneous application of the phytotoxic chemical
and safener (tank mixture).
[0054] The concentration of safener to be applied with respect to
the herbicide will depend substantially on the mode of application.
Where a field treatment is carried out either by using a tank
mixture with a combination of safener and herbicide or by separate
application of safener and herbicide, the ratio of safener to
herbicide will usually be from 1:100 to 1:1, preferably from 1:50
to 1:10.
[0055] In field treatment, 0.001 to 5.0 kg/ha, preferably 0.001 to
0.5 kg/ha, of safener, will usually be applied.
[0056] The concentration of herbicide is usually in the range from
0.001 to 10 kg/ha, but will preferably be from 0.005 to 5
kg/ha.
[0057] The novel compositions are suitable for all methods of
application commonly employed in agriculture, including
preemergence application, postemergence application and seed
dressing.
[0058] For seed dressing, 0.001 to 10 g of safener/kg of seeds,
preferably 0.05 to 2 g of safener/kg of seeds, will usually be
applied. If the safener is used in liquid form shortly before
sowing to effect soaking, then it is preferred to use safener
solutions that contain the active ingredient in a concentration of
1 to 10 000 ppm, preferably of 100 to 1000 ppm.
[0059] For application, it is preferred to process the compounds of
formula HI, or combinations of the compounds of formula II and the
herbicides of formula I, together with the assistants
conventionally employed in formulation technology, typically to
emulsifiable concentrates, coatable pastes, directly sprayable or
dilutable solutions, dilute emulsions, wettable powders, soluble
powders, dusts, granulates or microcapsules.
[0060] The formulations are prepared in known manner, e.g. by
homogeneously mixing and/or grinding the active ingredients with
extenders, typically with solvents or solid carriers.
Surface-active compounds (surfactants) can additionally be used for
preparing the formulations.
[0061] Suitable solvents may typically be: aromatic hydrocarbons,
preferably the fractions containing 8 to 12 carbon atoms, for
example 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, for example ethanol, ethylene glycol, 2-methoxyethanol
or 2-ethoxyethanol; ketones such as cyclohexanone; strongly polar
solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or
dimethyl formamide; as well as vegetable oils or epoxidised
vegetable oils such as epoxidised coconut oil or soybean oil; or
water.
[0062] The solid carriers typically used for dusts and dispersible
powders are usually natural mineral fillers such as calcite,
talcum, kaolin, montmorillonite or attapulgite. To improve the
physical properties it is also possible to add highly dispersed
silicic acid or highly dispersed absorbent polymers. Suitable
granulated adsorptive carriers are porous types, including pumice,
broken brick, sepiolite or bentonite; and suitable nonsorbent
carriers are materials such as calcite or sand. In addition,
innumerable pregranulated materials of inorganic or organic origin
may be used, especially dolomite or pulverised plant residues.
[0063] Depending on the safener, and usually also on the herbicide,
suitable surface-active compounds are nonionic, cationic and/or
anionic surfactants having good emulsifying, dispersing and wetting
properties. Surfactants will also be understood as comprising
mixtures of surfactants.
[0064] Suitable anionic surfactants may be water-soluble soaps as
well as water-soluble synthetic surface-active compounds.
[0065] Suitable soaps are the alkali metal salts, alkaline earth
metal salts, ammonium salts 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 mixtures of natural fatty acids
which can be obtained, inter alia, from coconut oil or tallow oil.
Further suitable soaps are also the fatty acid methyl taurin
salts.
[0066] More often, however, so-called synthetic surfactants are
used, especially fatty sulfonates, fatty sulfates, sulfonated
benzimidazole derivatives or alkylarylsulfonates.
[0067] The fatty alcohol sulfonates or sulfates are usually in the
form of alkali metal salts, alkaline earth metal salts, ammonium
salts or substituted ammonium salts, and they 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 ligninsulfonic
acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates
obtained from natural fatty acids. These compounds also comprise
the salts of sulfated and sulfonated fatty alcohol/ethylene oxide
adducts. The sulfonated benzimidazole derivatives preferably
contain two sulfonic acid groups and one fatty acid radical
containing 8 to 22 carbon atoms. Illustrative examples of
alkylarylsulfonates are the sodium, calcium or triethanolamine
salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic
acid, or of a condensate of naphthalenesulfonic acid and
formaldehyde.
[0068] Corresponding phosphates, typically salts of the phosphoric
acid ester of an adduct of p-nonylphenol with 4 to 14 mol of
ethylene oxide, or phospholipids, are also suitable.
[0069] Nonionic surfactants are preferably polyglycol ether
derivatives of aliphatic or cycloaliphatic alcohols or of 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.
[0070] Further suitable nonionic surfactants are the water-soluble
polyadducts of polyethylene oxide with polypropylene glycol,
ethylenediaminopolypropylene glycol and alkylpolypropylene glycol
containing 1 to 10 carbon atoms in the alkyl chain, which
polyadducts 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.
[0071] Illustrative examples of nonionic surfactants are
nonylphenol polyethoxylates, polyethoxylated castor oil,
polyadducts of polypropylene and polyethylene oxide, tributylphenol
polyethoxylate, polyethylene glycol and octylphenol
polyethoxylate.
[0072] Fatty acid esters of polyoxyethylene sorbitan are also
suitable nonionic surfactants, typically polyoxyethylene sorbitan
trioleate.
[0073] Cationic surfactants are preferably quaternary ammonium
salts carrying, 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, for example stearyl
trimethylammonium chloride or benzyl
bis(2-chloroethyl)ethylammonium bromide.
[0074] The surfactants customarily employed in the art of
formulation are described, inter alia, in "Mc Cutcheon's Detergents
and Emulsifiers Annual", MC Publishing Corp., Glen Rock, N.J.,
1981, H. Stache, "Tensid-Taschenbuch" (Handbook of Surfactants),
Carl Hanser Verlag, Munich/Vienna 1981, and J. Ash, "Encyclopedia
of Surfactants", Vol. I-III, Chemical Publishing Co., New York,
1980-81.
[0075] The agrochemical formulations will usually contain from 0.1
to 99% by weight, preferably from 0.1 to 95% by weight, of safener
of formula II or mixture of safener and herbicide, from 1 to 99.9%
by weight, preferably from 5 to 99.8% by weight, of a solid or
liquid formulation assistant, and from 0 to 25% by weight,
preferably from 0.1 to 25% by weight, of a surfactant.
[0076] Whereas it is preferred to formulate commercial products as
concentrates, the end user will normally use dilute
formulations.
[0077] The compositions may also contain further ingredients such
as stabilisers, antifoams, viscosity regulators, binders,
tackifiers, as well as fertilisers or other chemical agents, e.g.
commercial chloroacetanilides such as Frontier, Metazachlor,
Acetochlor, Alachlor, Metolachlor or Butachlor, for achieving
special effects.
[0078] Different methods and techniques may suitably be used for
applying compounds of formula II or compositions containing them
for protecting cultivated plants from the harmful effects of the
herbicide of formula I, typically the following:
[0079] i) Seed Dressing
[0080] a) Dressing the seeds with a wettable powder formulation of
the compound of formula II by shaking in a vessel until the safener
is uniformly distributed on the surface of the seeds (dry
treatment), using up to c. 1 to 500 g of compound of formula II (4
g to 2 kg of wettable powder) per 100 kg of seeds.
[0081] b) Dressing seeds with an emulsifiable concentrate of the
compound of formula II by method a) (wet treatment).
[0082] c) Dressing by immersing the seeds in a mixture containing
100-1000 ppm of compound of formula II for 1 to 72 hours, leaving
them wet or subsequently drying them (seed soaking).
[0083] Seed dressing or treatment of the germinated seedlings are
naturally the preferred methods of application, as the safener
treatment is fully concentrated on the target crop. Usually 1 to
1000 g, preferably 5 to 250 g, of safener is used per 100 kg of
seeds. However, depending on the method employed, which also
permits the use of other chemical agents or micronutrients, plus or
minus deviations from the indicated limiting concentrations are
possible (repeat dressing).
[0084] ii) Application from a Tank Mixture
[0085] A liquid formulation of a mixture of safener and herbicide
(reciprocal ratio from 10:1 to 1:100) is used, the concentration of
herbicide being from 0.01 to 10 kg/ha. This tank mixture is applied
before or after sowing.
[0086] iii) Application in the Furrow
[0087] The safener formulated as emulsifiable concentrate, wettable
powder or granulate is applied to the open furrow in which the
seeds have been sown. After covering the furrow, the herbicide is
applied pre-emergence in conventional manner.
[0088] iv) Controlled Release of Safener
[0089] A solution of the compound of formula II is applied to
mineral granulate substrates or polymerised granulates
(urea/formaldehyde) and allowed to dry. A coating may additionally
be applied (coated granulates) which permits controlled release of
the safener over a specific period of time.
[0090] The following examples illustrate the activity of the novel
compositions in more detail.
FORMULATION EXAMPLES FOR MIXTURES OF THE COMPOUND OF FORMULA I AND
A SAFENER OF FORMULA II (THROUGHOUT, PERCENTAGES ARE BY WEIGHT)
[0091]
3 F1. Emulsifiable concentrates a) b) c) d) compound mixture 5% 10%
25% 50% Ca dodecylbenzenesulfonate 6% 8% 6% 8% polyethoxylated
castor oil 4% -- 4% 4% (36 mol EO) octylphenol polyethoxylate -- 4%
-- 2% (7-8 mol EO) cyclohexanone -- -- 10% 20% mixture of aromatic
hydrocarbons 85% 78% 55% 16% C.sub.9-C.sub.12
[0092] Emulsions of any desired concentration can be prepared from
such concentrates by dilution with water.
4 F2. Solutions a) b) c) d) compound mixture 5% 10% 50% 90%
1-methoxy-3-(3-methoxypropoxy)- -- 20% 20% -- propane polyethylene
glycol 400 20% 10% -- -- N-methyl-2-pyrrolidone -- -- 30% 10%
mixture of aromatic hydrocarbons 75% 60% -- -- C.sub.9-C.sub.12
[0093] The solutions are suitable for use as microdrops.
5 F3. Wettable powders a) b) c) d) compound mixture 5% 25% 50% 80%
sodium ligninsulfonate 4% -- 3% -- sodium laurylsulfate 2% 3% -- 4%
sodium diisobutylnaphthalene -- 6% 5% 6% sulfonate octylphenol
polyethoxylate -- 1% 2% -- (7-8 mol EO) highly dispersed silica 1%
3% 5% 10% kaolin 88% 62% 35% --
[0094] The compound mixture is throughly mixed with the adjuvants
and this mixture is ground in a suitable mill to give wettable
powders which can be diluted with water to give suspensions of any
desired concentration.
6 F4. Coated granulates a) b) c) compound mixture 0.1% 5% 15%
highly dispersed silica 0.9% 2% 2% inorganic carrier 99.0% 93% 83%
(.O slashed. 0.1-1 mm) e.g. CaCO.sub.3 or SiO.sub.2
[0095] The compound mixture is dissolved in methylene chloride, the
solution is sprayed on to the carrier, and the solvent is removed
under vacuum.
7 F5. Coated granulates a) b) c) compound mixture 0.1% 5% 15%
polyethylene glycol 200 1.0% 2% 3% highly dispersed silica 0.9% 1%
2% inorganic carrier 98.0% 92% 80% (.O slashed. 0.1-1 mm) e.g.
CaCO.sub.3 or SiO.sub.2
[0096] The finely ground compound mixture is uniformly applied in a
mixer to the kaolin moistened with polyethylene glycol. Non-dusty
coated granulates are obtained in this manner.
8 F6. Extruder granulates a) b) c) d) compound mixture 0.1% 3% 5%
15% sodium ligninsulfonate 1.5% 2% 3% 4% carboxymethyl cellulose
1.4% 2% 2% 2% kaolin 97.0% 93% 90% 79%
[0097] The compound mixture is mixed with the adjuvants and the
mixture is moistened with water. This mixture is extruded and then
dried in a stream of air.
9 F7. Dusts a) b) c) compound mixture 0.1% 1% 5% talcum 39.9% 49%
35% kaolin 60.0% 50% 60%
[0098] Ready for use dusts are obtained by mixing the compound
mixture with the carriers and milling the mixture so obtained on a
suitable mill.
10 F8. Suspension concentrates a) b) c) d) compound mixture 3% 10%
25% 50% ethylene glycol 5% 5% 5% 5% nonylphenol polyethoxylate --
1% 2% -- (15 mol EO) sodium ligninsulfonate 3% 3% 4% 5%
carboxymethyl cellulose 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%
[0099] The finely ground compound mixture is intimately mixed with
the adjuvants to give a suspension concentrate from which
suspensions of any desired concentration can be prepared by
dilution with water.
EXAMPLE B 1
Preemergence Phytoxic Action of the Herbicide of Formula I and of
the Mixtures of Herbicide and Safener of Formula II on Maize
[0100] Maize is sown in standard soil in plastic pots. Immediately
after sowing, the pots are sprayed with an aqueous suspension of
the test substances (500 l of water/ha) prepared from one of the
above formulations 1 to 8. The concentration of herbicide of
formula I is 4000, 3000 and 2000 g/ha. The safener No. 1.006 is
applied in a ratio to the herbicide of 1:18, 1:24 and 1:30. The
test plants are afterwards cultivated in a greenhouse under optimum
conditions. The phytotoxic action of the herbicide on the maize
(percentage phytotoxicity) is evaluated after a test duration of 22
days.
[0101] a) Concentration of Herbicide: 4000 g/ha
11 Ratio of herbicide to safener % Phytotoxicity no safener 65 18:1
20 24:1 20 30:1 15
[0102] b) Concentration of Herbicide: 2000 g/ha
12 Ratio of herbicide to safener % Phytotoxicity no safener 55 18:1
0 24:1 0 30:1 0
[0103] c) Concentration of Herbicide: 2000 g/ha
13 Ratio of herbicide to safener % Phytotoxicity no safener 25 18:1
0 24:1 0 30:1 0
[0104] The results show that the compounds of formula II are able
to reduce markedly the damage caused by the herbicide to the
cultivated plants.
* * * * *