Herbicidal compositions

Abstract

herbicide combinations comprising an effective amount of components (A) and (B), where

component (A) is/are one or more herbicides of the formula (I) or salts thereof,

##STR00001##
in which

• R¹ is H or a group of the formula CZ¹Z²Z³, where Z¹, Z² and Z³ are as defined in claim 1, R² and R³ are each H, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl having in each case up to 4 carbon atoms or acyl, R⁴ is H, (C₁-C₆)-alkyl or (C₁-C₆)-alkoxy;
• R⁵, R⁶, R⁷ and R⁸ are each H, (C₁-C₄)-alkyl, (C₁-C₃)-haloalkyl, halogen, (C₁-C₃)-alkoxy, (C₁-C₃)-haloalkoxy or cyano;
• A is CH₂ or O or a direct bond, and
• the component (B) is one or more herbicides from the group of compounds consisting of
• (B1) thiencarbazone, tembotrione, SYN-523, pyroxsulam, penoxsulam, SYN-449,
• (B2) pyrasulfotole, trifloxysulfuron, saflufenacil, aminopyralid, ethofumesate, aminocyclopyrachlor and
• (B3) pyroxasulfone (KIH-485)
  are suitable for controlling harmful plants or for regulating the growth of plants.

Description

In this formula:

• • A=action of active compound (A) in % at an application rate of a g of AS/ha;
  • B=action of active compound (B) in % at an application rate of b g of AS/ha;
  • E=expected value of the action of the combination (A)+(B) in % at the combined application rate a+b g of AS/ha.

The data observed in the experiments show, at suitably low dosages, an action of the combinations which exceeds the expected values according to Colby.

2. Post-emergence Herbicidal Action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy loam in pots, covered with soil and grown in the greenhouse under good growth conditions (temperature, atmospheric humidity, water supply). Three weeks after sowing, the test plants are treated in the three-leaf stage with the compositions according to the invention. The compositions according to the invention, formulated as wettable powders or emulsion concentrates, are sprayed onto the green plant parts in various dosages using an application rate of 300 to 800 l of water/ha (converted). After the test plants have remained in the greenhouse under optimum growth conditions for about 3 to 4 weeks, the effect of the preparations is scored visually in comparison with untreated controls (scoring as in Example 1). The compositions according to the invention also have good herbicidal post-emergence action against a broad spectrum of economically important weed grasses and broad-leaf weeds.

Here, effects of the combinations according to the invention are frequently observed which exceed the formal total of the effects of the herbicides when these are applied by themselves. The observed values for the tests show, at suitably low dosages, an effect of the combinations which exceeds the expected values according to Colby (cf. scoring in Example 1).

3. Pre- and Post-emergence Herbicidal Action (Outdoor Trials)

Corresponding to the greenhouse experiments of sections 1 and 2, the tests were carried out in the open on plots. Scoring was carried out analogously to the tests in sections 1 and 2.

4. Herbicidal Action and Crop Plant Tolerance (Outdoor Trials)

Crop plants were grown in the open on plots under natural outdoor conditions, and seeds or rhizome pieces of typical harmful plants were laid out or the natural weed growth was utilized. Treatment with the compositions according to the invention was carried out after the harmful plants had emerged and the crop plants were, generally, at the 2- to 4-leaf stage; in some cases (as stated), application of individual active compounds or active compound combinations was carried out pre-emergence or as a sequential treatment partly pre-emergence and/or post-emergence.

In the case of plantation crops, it was generally only the soil between the individual crop plants that was treated with the active compounds.

After the application, for example 2, 4, 6 and 8 weeks after application, the effect of the preparations was scored visually by comparison with untreated controls (cf. scoring in Example 1). In the outdoor trial as well, the compositions according to the invention have synergistic herbicidal activity against a broad spectrum of economically important weed grasses and broad-leaf weeds. The comparison showed that the combinations according to the invention in most cases have a higher, in some cases a considerably higher, herbicidal activity than the total of the activities of the individual herbicides, thus indicating synergism. Moreover, the effects in essential phases of the scoring period were above the expected values according to Colby (cf. scoring in Example 1), also indicating synergism. In contrast, the crop plants were, as a consequence of the treatments with the herbicidal compositions, damaged only to a small degree, if at all.

5. Specific Test Examples

The following abbreviations are used in the description and the tables below:

• g of AS/ha=grams of active substance (=100% active compound) per hectare;
• the total of the activities of the individual applications is given as E^A;
• the expected values according to Colby are in each case given as E^C;
  Example 5.1

Certain combinations were tested for their herbicidal activity in accordance with the general example 1 (pre-emergence method). The results are summarized in Table 4.

TABLE 4
Active	Application rate	Herbicidal action [%] against
compound(s)	[g of AS/ha]	Ipomoea hederifolia
(A21)	0.5	45
	0.2	0
(B1.1.2)	2.0	50
	0.5	5
(A21) + (B1.1.2)	0.2 + 0.5	67
		(EA = 0 + 5, EC = 0 + 5)
Abbreviations and conditions in Table 4:
Conditions: pot trials/greenhouse, application by the pre-emergence method, evaluation 27 days after treatment
AS = active substance (based on 100% of active compound)
(A21) = compound (A21) from Table 1 = 2-amino-4-[(1R,2S)-2,6-dimethyl-indan-1-ylamino]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine
(B1.1.2) = thiencarbazone-methyl = methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylsulfamoyl]-5-methylthiophene-3-carboxylate

Example 5.2

Certain combinations were tested for their herbicidal activity in accordance with the general example 1 (pre-emergence method). The results are summarized in Table 5.

TABLE 5
Active	Application rate	Herbicidal action [%] against
compound(s)	[g of AS/ha]	Erodium cicutarium
(A21)	0.8	25
	0.2	0
(B1.2.1)	50	30
(A21) + (B1.2.1)	0.2 + 50	75
		(EA = 0 + 30, EC = 0 + 30)
(B1.3)	15	65
(A21) + (B1.3)	0.2 + 15	75
		(EA = 0 + 65, EC = 0 + 65)
(B1.4.1)	5	50
(A21) + (B1.4.1)	0.2 + 5	68
		(EA = 0 + 50, EC = 0 + 50)
(B1.6.1)	30	55
(A21) + (B1.6.1)	0.2 + 30	75
		(EA = 0 + 55, EC = 0 + 55)
Abbreviations and conditions in Table 5:Conditions: in each case pot trials/greenhouse, application by the pre-emergence method, evaluation 28 days after treatment
AS = active substance (based on 100% active compound)(A21) = compound (A21) from Table 1 = 2-amino-4-[(1R,2S)-2,6-dimethyl-indan-1-ylamino]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine
(B1.2.1) = tembotrione = 2-{2-chloro-4-mesyl-3-[(2,2,2-trifluoroethoxy)methyl]-benzoyl}cyclohexane-1,3-dione
(B1.3) = ethyl [[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenoxy]-2-pyridinyl]oxy]acetate
(B1.4.1) = N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide
(B1.6.1) = 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-trifluoromethyl-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one

Example 5.3

Certain combinations were tested for their herbicidal activity in accordance with the general example 1 (pre-emergence method). The results are summarized in Table 6.

TABLE 6
Active	Application rate	Herbicidal action [%] against
compound(s)	[g of AS/ha]	Geranium dissectum
(A21)	1.2	20
	0.3	5
(B2.1.1)	30	20
(A21) + (B2.1.1)	0.3 + 30	65
		(EAA = 5 + 20, EC = 24)
(B2.2.2)	25	45
(A21) + (B2.2.2)	0.3 + 25	60
		(EA = 5 + 45, EC = 47.8)
(B2.3.1)	50	65
(A21) + (B2.3.1)	0.3 + 50	80
		(EA 5 + 65, EC = 66.8)
(B2.4.1)	75	50
(A21) + (B2.4.1)	0.3 + 75	85
		(EA = 5 + 50, EC = 52.5)
(B2.5)	300	35
(A21) + (B2.5)	0.3 + 300	55
		(EA = 5 + 35, EC = 38.3)
(B2.6.1)	100	65
(A21) + (B2.6.1)	0.3 + 100	95
		(EA = 5 + 65, EC = 66.8)
(B3.1)	50	50
(A21) + (B3.1)	0.3 + 50	75
		(EA = 5 + 50, EC = 52.5)
Abbreviations and conditions in Table 6:
Conditions: in each case pot trial/greenhouse, application by the pre-emergence method, evaluation 28 days after treatment
AS = active substance (based on 100% active compound)
(A21) = compound (A21) from Table 1 = 2-amino-4-[(1R,2S)-2,6-dimethyl-indan-1-ylamino]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine
(B2.1.1) = pyrasulfotole = (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)-[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
(B2.2.2) = trifloxysulfuron sodium salt = 1-(4,6-dimethoxypyrimidin-2-yl)-3-[3-(2,2,2-trifluoroethoxy)-2-pyridylsulfonyl]urea sodium salt
(B2.3.1) = saflufenacil = 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide
(B2.4.1) = aminopyralid = 4-amino-3,6-dichloropyridine-2-carboxylic acid
(B2.5) = ethofumesate = (RS)—O-(2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl) methanesulfonate
(B2.6.1) = aminocyclopyrachlor = 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid
(B3.1) = pyroxasulfone = 3-[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole

Claims

1. A herbicide combination comprising:

an effective amount of components (A) and (B);

wherein component A includes one or more herbicidally active compounds (A) selected from the group consisting of:

2. The herbicide combination as claimed in claim 1;

wherein active compound components (A) and (B) are present in a weight ratio of from 1:100000 to 2000:1.

3. The herbicide combination as claimed in claim 1;

wherein active compound components (A) and (B) are present in a weight ratio of from 1:40000 to 750:1.

4. The herbicide combination as claimed in claim 1;

which comprises one or more further components from the group comprising crop protection agents.

5. A herbicidal composition which comprises:

the herbicide combination as claimed in claim 1; and

one or more additives customary in crop protection.

6. A method for controlling harmful plants which comprises:

applying a synergistically effective amount of the active compound components of the herbicide combination as defined in claim 1 together or separately, by the pre-emergence method, by the post-emergence method, or by the pre-emergence and the post-emergence method, onto the plants, parts of plants, plant seeds, or the area where the plants grow.

7. The method as claimed in claim 6;

wherein the herbicide component (A) is applied in an application amount of from 0.01 to 2000 g of active substance per hectare and the herbicide component (B) is applied in an application amount of from 0.01 to 1000 g of active substance per hectare.

8. The method as claimed in claim 6 for the control of harmful plants on non-crop land or in plantation crops.

9. The method as claimed in claim 6;

wherein the active compounds of the herbicide combination are applied in the form of a herbicidal composition which comprises one or more additives customary in crop protection, if appropriate after dilution with water.

10. The herbicide combination according to claim 1, wherein component (B) is (B1.2.1) tembotrione.

11. The herbicide combination according to claim 1, wherein component (B) is (B1.3) ethyl [3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenoxyl-2-pyridinyl]oxy]acetate (SYN-523).

12. The herbicide combination according to claim 1, wherein component (B) is (B1.4.1) pyroxsulam.

13. The herbicide combination according to claim 1, wherein component (B) is (B1.6.1) 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-trifluoromethyl-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (SYN-449).

14. The herbicide combination according to claim 1, wherein component (B) is (B2.2.2) trifloxysulfuron sodium salt.

15. The herbicide combination according to claim 1, wherein component (B) is (B2.3.1) saflufenacil.

16. The herbicide combination according to claim 1, wherein component (B) is (B2.4.1) aminopyralid.

17. The herbicide combination according to claim 1, wherein component (B) is (B2.5) ethofumesate.

18. The herbicide combination according to claim 1, wherein component (B) is (B3.1) pyroxasulfone (KIH-485).