WO1993008689A1

WO1993008689A1 - Synergistic herbicidal compositions

Info

Publication number: WO1993008689A1
Application number: PCT/EP1992/002535
Authority: WO
Inventors: Gerhard Johann; Richard Rees
Original assignee: Schering Aktiengesellschaft
Priority date: 1991-11-05
Filing date: 1992-10-30
Publication date: 1993-05-13
Also published as: TW224932B; IL103626A0; FI942050A0; JPH07502498A; AU2920492A; BR9206712A; FI942050L; HUT66872A; RU94021656A; EP0612213A1; HU9401307D0; CA2122898A1; ZA928540B; DE4136740A1; CN1073071A

Abstract

There is described new herbicidal compositions with synergistic activity which comprises a mixture of 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin-1,3-one and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D (V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaquin (XXII) and imazethapyr (XXIII).

Description

SYNERGISTIC HERBICIDAL COMPOSITIONS

This invention relates to a new herbicidal composition having synergistic activity comprising a mixture of

2-[7-fluoro-3,4-dihydro-3-oxb-4-(2-propynyl)- 2H-1,4-benzoxazin-6-yl]perhydxoimidazo[l,5-a]pyridin- 1,3-one and another selective herbicide and its use for combating weeds in crops.

The herbicidal activity of 2-[7-fluoro-3,4-dihydro-3-oxo- 4-(2-propγnyl)-2H-1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin-1,3-one is already known

(EP 311 135). This compound has the following chemical structure (I)

It has now been found that herbicidal compositions which comprise, as active components, a mixture of

2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin-1,3-one and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D (V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X) and sethoxydim (XI) as well as metribuzin (XII), linuron

(XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor (XVIII), metolachlor (XIX), trifluralin (XX), chlorimuron-ethyl (XXI), imazaguin (XXII) and imazethapyr (XXIII), broaden the spectrum of weeds that can be controlled and show an increase in herbicidal activity in comparison with the individual components without losing the selectivity properties in agricultural crops.

Glyphosate is the common name for N-(phosphonomethyl)- glycine;

sulfometuron-methyl is the common name for methyl

2-(4,6-dimethylpyridin-2-ylcarbamoylsulfamoyl)benzoate; imazapyr is the common name for 2-(4-isopropyl-4-methyl-5- oxo-2-imidazolin-2-yl)-nicotinic acid;

2,4-D is the common name for 2-(4-chloro-2-methylphenoxy)acetic acid;

dicamba is the common name for 3,6 dichloro-2-methoxybenzoic acid;

diuron is the common name for 3-(3,4-dichlorophenyl)-1,1- dimethylurea;

oxyfluorfen is the common name for 2-chloro- α,α,α-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether;

glufosinate ammonium is the common name for ammonium

4-[hydroxy(methyl)phosphinoyl]-DL-homoalaninate;

amitrole is the common name for 1H-1,2,4-triazol-3-ylamine;

sethoxydim is the common name for (±)-(EZ)-2-(1-ethoxyiminobutyl)-5-[2-(ethylthio)propyl]-3-hydroxycyclohex-2-enone;

metribuzin is the common name for 4-amino-6-tert.-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one;

linuron is the common name for 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea;

acifluorfen is the common name for 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid;

lactofen is the common name for (±) -2-ethoxy-1-ethyl-2-oxoethyl 5-[chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoate;

fomesafen is the common name for 5-[2-chloro- 4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide;

pendimethalin is the common name for N-(1-ethylpropyl)- 3,4-dimethyl-2,6-dinitroaniline;

alachlor is the common name for 2-chloro-2',6'-diethyl- N-methoxymethylacetanilide;

metolachlor is the common name for 2-chloro-6'-ethyl- 2'-methy1-N-(2-methoxy-1-methylethyl)acetanilide;

trifluralin is the common name for 2,6-dinitro- N,N-dipropyl-4-(trifluoromethyl)aniline;

chlorimuron-ethyl is the common name for ethyl

2-(4-chloro-6-methoxypyrimidin-2-ylcarbamoylsulfamoyl)- benzoate;

imazaguin is the common name for (±)-2-[4,5-dihydro- 4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazole-2-yl]- 5-ethyl-3-pyridinecarboxylic acid; and

imazethapyr is the common name for (±)-2-[4,5-dihydro- 4-methyl-4-(1-methylethyl)-5-oxo-1H-2-yl]-3-quinoline carboxylic acid.

All these herbicides are described in the "Pesticide Manual", ninth edition, 1991, published by the British Crop Protection Council, London.

The combinations of the invention are suitable for the control of important annual and perennial weeds,

especially in plantation and permanent crops, such as for example in fruit, wine, citrus, forests and ornamental cultivations, in arable land outside the vegetation time (for example stubble treatment), as well as in the industrial area including highways and railways. Further uses are for the control of important weeds in a range of crops, such as for example soya beans. The combination of active ingredients of the invention can used for example against the following plant species:

Dicotyledonous weeds of the species Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga,

Chenopodium, Brassica, Urtica, Senecio, Amaranthus,

Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola,

Galeopsis, Papaver, Centaurea and Chrysanthemum.

Monocotyledonous weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron (= Elymus), Sagittaria, Monocharia, Fimbristylis, Eleocharis,

Ischaemum and Apera.

The combinations of I with II-XI can be applied pre- emergently, and the combinations of I with XII-XXIII can be applied post-emergently. The rate of use lies between

0.001 and 5 kg/ha of the mixture, depending on the use. By using the mixtures for control of weeds the amount of herbicide needed can be generally reduced. The weight ratio of component I) to the other component is generally between 50:1 and 1:100.

The compositions of the invention can also be used in admixture with other active agents for example other plant-protection agents or pesticides, depending on the particular need.

An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents and oils. Such additives may allow a decrease in the dose.

The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts,

granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants. Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide,

dimethylformamide and other mineral-oil fractions and plant oils.

Suitable solid carriers include mineral earths, e.g.

bentonite, silica gel, talc, kaolin, attapulgite,

limestone, silicic acid and plant products, e.g. flours. As surface-active agents there can be used for example calcium lignosulfonate, polyoxyethylenealkylphenyl ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, as well as substituted benzenesulfonic acids and their salts.

The percentage of the active ingredient(s) in the various preparations can vary within wide limits. For example, the compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.

The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1,000 1/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.

The preparation of these formulations can be carried out in known manner, for example by milling or mixing

processes. Optionally, individual components can be mixed just before use for example by the so-called commonly used tank-mixing method.

The following Examples illustrate the use of compositions of the invention.

The calculation of synergistic effect is carried out according to S R Colby "Calculating Synergistic and

Antagonistic Response to Herbicide Combinations" , Weeds, 15/1, 1967 pages 20 to 22. In this the following formula was used:

in which X = the herbicidal activity (%) of substance A at a rate of p g/ha.

Y = the herbicidal activity (%) of substance B at a rate of q g/ha., and

E = the expected additive activity of the

herbicide (%) of the substances A + B at a rate of p + q g/ha.

If the observed value is greater than the value of E calculated according to Colby, the combination shows synergistic activity. Experiments

In a greenhouse the plant species shown in tables A-K were treated post-emergently with the components at the stated rates. The compositions were diluted with 500 litres of water and sprayed evenly over the plants. Two weeks after treatment the herbicidal effect was evaluated.

Table A

Mixtures of I with glyphosate (II)

Rate Herbicidal E ( according

(g/ha) activity (%) to Colby)

Amaranthus retro flexus

I 1 80

II 50 5

I + II 1 + 50 85 ( 81 )

Cyperus esculentus

I 4 40

II 400 5

I + II 4 + 400 90 ( 43 )

Elymus repens

I 4 50

II 400 40

III 4 + 400 85 ( 70 ) Table B

Mixtures of I with sulfometuron-methyl (III)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Component Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Brachiaria mutica

I 8 10

III 2 50

I + III 8 + 2 75 (59) Sesbania exaltata

I 4 20 III 2 60 I + III 4 + 2 75 (68)

Bromus sp.

I

III

I + III 8 + 4 75 (68)

Table C

Mixtures of I with imazapyr (IV)

Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Setaria viridis

I 1 30

IV 2 80 I + IV 1 + 2 90 (86)

Sorghum halepense

I ⁸ 70

IV 1 20

I + IV 8 + 1 90 (76)

Cyperus esculentus

I 4 80

IV 4 10

I + IV 4 + 4 98 (82)

Table D

Mixtures of I with 2,4-D (V)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Bidens pilosa

I 4 60

V 100 0

200 10

I + V 4 + 100 80 (60)

4 + 200 85 (64)

Sesbania exaltata

I 4 40

8 80

V 100 0

I + V 4 + 100 90 (40)

8 + 100 98 (80)

Amaranthus retroflexus

I 2 70

V 50 10

200 20

I + V 2 + 50 90 (73)

2 + 200 90 (76) Table E

Mixtures of I with dicamba (VI)

Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Sesbania exaltata

I 1 20

VI 25 70

I + VI 1 + 25 90 (76)

Bidens pilosa

I 1 40

VI 25 60

I + VI 1 + 25 85 (76)

Table F

Mixtures of I with diuron (VII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sesbania exaltata

I 0.5 0

1 0

2 30

4 90

VII 50 5

100 80

I + VII 0.5 + 100 95 (80)

1 +• 100 95 (80)

2 + 50 75 (34)

4 + 50 95 (91)

Bidens pilos a

I 2 50

4 65

8 80

VII 25

I + VII 2 + 25 85 (50)

4 + 25 99 (65)

8 + 25 100 (80)

Cyperus esculentus

I 8 40

VII 100 0

200 5

I + VII 8 + 100 70 (40)

8 + 200 80 (43)

Setaria viridis

I 1 5

VII 100 70

I + VII 1 + 100 97 (72) Table G

Mixtures of I with oxyfluorfen (VIII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sesbania exaltata

I 1 20

2 50

VIII 2 30

I + VIII 1 + 2 70 (49)

2 + 2 90 (65)

Amaranthus retroflexus

I 1 60

VIII 2 70

I + VIII 1 + 2 98 (88)

Table H

Mixtures of I with glufosinate-ammonium (IX)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Setaria viridis

4 20

I

80 60

IX

(68)

I + IX 4 + 80 80

Brachiaria. mutica

8 20

I

80 20

IX

I + IX 8 + 80 95 (36)

Sorghum halepense

I 8 50

IX 40 0

I + IX 50 90 (50)

Sesbania exaltata

I 2 60

IV 80 0

I + IX 2 + 80 98 (60) Table I

Mixtures of I with amitrole (X)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Setaria viridis

I 4 20 X 200 60 I + X 4 + 200 80 (68)

Bracharia mutica

I 4 0

8 5

X 200 30

I + X 4 + 200 70 (30)

8 + 200 95 (33)

Bidens Dilosa

I 4 70

X 50 20

I + X 4 + 50 85 (76)

Sesbania exa Itata

I 1 30

2 50

X 25 5

50 30

I + X 1 + 25 70 (33)

1 + 50 85 (51)

2 + 25 90 (53)

2 + 50 95 (65) Table K

Mixtures of I with sethoxydim (XI)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Setaria viridis

I 4 10

XI 100 70

I + XI 4 + 100 98 (73)

Brachiaria mutica

I 8 15

XI 50 80

I + XI 8 + 50 95 (83)

Bromus sp.

I 2 10

XI 200 60

I + XI 2 + 200 85 (64)

Experiments

In a greenhouse the plant species shown in tables L-W were treated pre-emergently with the components at the stated rates. The compositions were diluted with 500 litres of water and sprayed evenly over the soil. Two weeks after treatment the herbicidal effect was evaluated.

Table L

Mixtures of I with metribuzin (XII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Soiabohne

I 4 0

8 0

XII 12,5 0

50 0

100 5

I + XII 4 + 12,5 5 (0)

8 + 12,5 5 (0)

4 + 50 0 (0)

8 + 50 5 (0)

4 + 100 5 (5)

8 + 100 10 (5)

Ipomoea purpurea

I 8 60

XII 50 5

I + XII 8 + 50 70 (62)

Amaranthus retroflexus

I 4 10

8 10

XII 50 50

I + XII 4 + 50 98 (55)

8 + 50 98 (55) Table M

Mixtures of I with linuron (XIII)

Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Sojabohne

I 2 0

8 0

XIII 100 0

200 0

I + XIII 2 4- 100 0 (0)

2 + 200 0 (0)

8 + 100 0 (6)

8 + 200 5 (5)

Amaranthus retroflexus

I 8 20

XIII 100 0

I + XIII 8 + 100 80 (20)

Polygonum lapathiflolium

I 2 20

XIII 200 50

I + XIII 2 + 200 80 (60)

Setaria viridis

I 8 40

XIII 100 0

I + XIII 8 + 100 75 (40) Table N

Mixtures of I with acifluorfen (XIV)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Soiabohne

I 2 0

4 20

8 40

XIV 10 0

20 5

40 10

I + XIV 2 + 10 0 (0)

2 + 20 10 (5)

2 + 40 0 (10)

4 + 10 0 (20)

4 + 20 20 (24)

4 + 40 10 (27)

8 + 10 20 (40)

8 + 20 50 (43)

8 + 40 10 (46)

Ipomoea purpurea

I 8 70

XIV 10 0

20 10

I + XIV 8 + 10 85 (70)

8 + 20 95 (73)

Amaranthus retroflexus

I 4 40

XIV 40 30

I + XIV 4 + 40 90 (58)

Polygonum lapathifolium

I 8 80

XIV 10 0

I + XIV 8 + 10 95 (80) Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sorghum halepense

I 2 20

XIV 20 70

I + XIV 2 + 20 90 (76)

Digjtaria ischaemum

I 2 10

XIV 20 50

I + XIV 2 + 20 75 (55)

Table O

Mixtures of I with lactofen (XV)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 1 0

2 5

4 10

XV 20

I + XV 1 + 20 (0)

2 + 20 (5) 4 + 20 (10)

Amaranthus retroflexus

I 2 20

4 50

XV 20 40

I + XV 2 + 20 85 (52)

4 + 20 90 (70)

Polygonum lapathiflolium

I 2 40

4 70

XV 20 0

I + XV 2 + 20 90 (40)

4 + 20 95 (70)

Digitaria ischaemum

I 1 0

XV 20 50

I + XV 1 + 20 90 (50) Table P

Mixtures of I with fomesafen (XVI)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 2 0

4 20

8 20

XVI 10 10

40 20

80 20

I + XVI 2 + 10 0 (10)

2 + 40 30 (20)

2 + 80 20 (20)

4 + 10 10 (28)

4 + 40 10 (36)

4 + 80 20 (36)

8 + 10 20 (26)

8 + 40 20 (36)

8 + 80 20 (36)

Impomoea purpurea

I 8 60

XVI 40 20

80 40

I + XVI 8 + 40 90 (68)

8 + 80 95 (76)

Polygonum lapathiflolium

I 2 5

4 75

XVI 10 5

I + XVI 2 + 10 80 (8)

4 + 10 98 (77) Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Sorghum halepense

I 4 50

XVI 10 10

I + XVI 4 + 10 85 (55)

Digitaria ischaemum

I 4 50

XVI 10 30

I + XVI 4 + 10 90 (65)

Table O

Mixtures of I with pendimethalin (XVII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 2 0

4 0

8 0

XVII 25 0

200 0

I + XVII 2 + 25 0 (0)

4 + 25 0 (0)

8 + 25 0 (0)

2 + 200 0 (0)

4 + 200 0 (0)

8 + 200 0 (0)

Setaria viridis

I 6 0

XVII 200 75

I + XVII 8 + 200 98 (75)

Polygonum lapathiflolium

I 4 50

XVII 25 0

I + XVII 4 + 25 85 (50)

Amaranthus retroflexus

I 2 0

XVII 200 20

I + XVII 2 + 200 85 (20) Table R

Mixtures of I with alachlor (XVIII)

Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Sojabohne

I 4

8

XVIII 50

I + XVIII 4 + 50 (0)

8 + 50 (0)

Polygonum lapathifolium

I 4 20

8 80

XVIII 50

I + XVIII 4 + 50 95 (20)

8 + 50 100 (80)

Digitaria ischaeaum

I 4 0

8 40

XVIII 50 30

I + XVIII 4 + 50 90 (30)

8 + 50 97 (58)

Table S

Mixtures of I with metolachlor (XIX)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 4 0

8 0

XIX 50 0

100 0

I + XIX 4 + 50 0 (0)

8 + 50 0 (0)

4 + 100 (0)

8 + 100 (0)

Amaranthus retroflexus

I 8 40

XIX too 0

I + XIX 8 + 100 70 (40)

Setaria viridis

I 8 40

XIX 50 40

I + XIX 8 + 50 85 (64)

Digitaria ischaemum

I 4 20

8 30

XIX 50 60

I + XIX 4 + 50 90 (68)

8 + 50 95 (72) Table T

Mixtures of I with trifluralin (XX)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 2 0

4 10

8 10

XX 100 0

200 10

400 10

I + XX 2 + 100 0 (0)

4 + 100 0 (10)

8 + 100 10 (10)

2 + 200 0 (10)

4 + 200 10 (19)

8 + 200 10 (19)

2 + 400 0 (10)

4 + 400 0 (19)

8 + 400 10 (19)

Amaranthus retroflexus

I 4 50

XX 200 15

400 50

I + XX 4 + 200 90 (58)

4 + 400 95 (75)

Abutilon theoohrasti

I 4 80

XX 400 15

I + XX 4 + 400 90 (83) Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Polygonum lapathifolium

I 8 50

XX 200 0

400 10

I + XX 8 + 200 95 (50)

8 + 400 95 (55)

Panicum maximum

I 2 0

4 10

XX 100 90

I + XX 2 + 100 99 (90)

4 + 100 99 (91)

Table U

Mixtures of I with Chlorimuron-ethyl (XXI)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 8

XXI 4

8

I + XXI 8 + 4 (0)

8 + 8 (0)

Ipomoea purpurea

I 8 5

XXI 4 40

I + XXI 8 + 4 70 (43)

Bidens pilosa

I 8 0

XXI 8 70

I + XXI 8 + 8 80 (70)

Table V

Mixtures of I with imazaguin (XXII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 2 0

8 0

XXII 4 0

16 0

I + XXII 2 + 4 0 (0)

2 + 16 0 (0)

8 + 4 0 (0)

8 + 16 5 (0)

Ipomoea purporea

I 8 10

XXII 16 60

I + XXII 8 + 16 75 (64)

Amaranthus retroflexus

I 8 50

XXII 16 20

I + XXII 8 + 16 90 (60)

Polygonum lapathifolium

I 2 20

XXII 4 20

I + XXII 2 + 4 80 (36) Table W

Mixtures of I with imazethapyr (XXIII)

Rate Herbicidal E (according (g/ha) activity (%) to Colby)

Sojabohne

I 1 0

2 0

4 0

8 0

XXIII 2 0

4 0

8 10

16 0

I + XXIII 1 + 2 0 (0)

1 + 4 0 (0)

1 + 8 0 (10)

1 + 16 0 (0)

2 + 2 0 (0)

2 + 4 0 (0)

2 + 8 0 (10)

2 + 16 0 (0)

4 + 2 0 (0)

4 + 4 0 (0)

4 + 8 0 (10)

4 + 16 0 (0)

8 + 2 0 (0)

8 + 4 0 (0)

8 + 8 0 (10)

8 + 16 10 (0)

Ipomoea purpurea

I 8 15

XXIII 8 40

I + XXIII 8 + 8 70 (49 ) Rate Herbicidal E (according

(g/ha) activity (%) to Colby)

Amaranthus retroflexus

I 4 75

XXII I 2 0

4 0

I + XXIII 4 + 2 85 (75)

4 + 4 85 ( 75 ) Polygonum lapathifolium

I 4 70

XXIII 2 10

I + XXIII 4 + 2 95 (73)

Setaria viridis

I 1 0

2 0

XXIII 16 50

I + XXIII 1 + 16 75 (50)

2 + 16 80 (50)

Claims

1. A herbicidal composition which comprises, a mixture of 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)- 2H-1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridin- 1,3-one and a herbicide selected from the group consisting of glyphosate (II), sulfometuron-methyl (III), imazapyr (IV), 2,4-D (V), dicamba (VI), diuron (VII), oxyfluorfen (VIII), glufosinate-ammonium (IX), amitrole (X), sethoxydim (XI), metribuzin (XII), linuron (XIII), acifluorfen (XIV), lactofen (XV), fomesafen (XVI), pendimethalin (XVII), alachlor

(XVIII), metolachlor (XIX), trifluralin (XX),

chlorimuron-ethyl (XXI), imazaquin (XXII) and

imazethapyr (XXIII).

2. A composition according to claim 1, in which the

weight ratio of the mixture components is between 50:1 and 1:100.

3. A method of combating weeds which comprises applying post-emergently, a composition according to claim 1 or 2, which comprises component I and at least ome of the components II to XI.

4. A method of combating weeds which comprises applying pre-emergently, a composition according to claim 1 or 2, which comprises component I and at least ome of the components XII to XXIII.