Synergistic Herbicidal Combinations

Abstract

A herbicide combination comprising an effective amount of components (A) and (B), where (A) denotes one or more fatty acid derivatives of the formula (I),

##STR00001##

wherein R.sup.1 is an alkyl group containing 5 to 17 carbon atoms, which is linear or branched R.sup.2, R.sup.3 are, independently, hydrogen, methyl, ethyl or hydroxymethyl with the proviso that one of R.sup.2 and R.sup.3 is hydrogen and the other is different from hydrogen m, n are numbers from 0 to 17, with the proviso that m+n≥1 and m+n+p<18 where the different monomers can be arranged in statistical order, alternatingly or as a block copolymer, R.sup.4 is hydrogen or an alkyl group containing 1 to 10 carbon atoms, which is linear or branched, and (B) denotes one or more sulfonyl urea herbicides,
is particularly suitable for controlling unwanted vegetation.

Claims

1. A herbicide combination comprising an effective amount of components (A) and (B), where (A) is one or more fatty acid derivatives of the formula (I), ##STR00003## wherein R.sup.1 is an alkyl group containing 5 to 17 carbon atoms, which is linear or branched R.sup.2, R.sup.3 are, independently, hydrogen, methyl, ethyl or hydroxymethyl with the proviso that one of R.sup.2 and R.sup.3 is hydrogen and the other is different from hydrogen m, n are numbers from 0 to 17, with the proviso that m+n≥1 and m+n+p<18 where the different monomers can be arranged in statistical order, alternatingly or as a block copolymer, R.sup.4 is hydrogen or an alkyl group containing 1 to 10 carbon atoms, which is linear or branched, and (B) is one or more sulfonyl urea herbicides.

2. The herbicide combination as claimed in claim 1, wherein R.sup.1 is an alkyl group containing 5 to 13 carbon atoms, which is linear or branched; R.sup.2, R.sup.3 are, independently, hydrogen, methyl, ethyl or hydroxymethyl; m, n are numbers from 0 to 12, with the proviso that m+n>4, and m+n<12 where the different monomers can be arranged in statistical order, alternatingly or as a block copolymer, and R.sup.4 is a methyl group.

3. The herbicide combination as claimed in claim 1, wherein R.sup.1 is a linear alkyl group R.sup.1 is an alkyl group with 5 to 11, R.sup.2, R.sup.3 are hydrogen, methyl or ethyl, and m is a number from 0 to 5.

4. The herbicide combination as claimed in claim 1, wherein formula (I) m+n is >4.

5. The herbicide combination as claimed in claim 1, wherein formula (I) m is 0, and n is a number from >4.

6. The herbicide combination as claimed in claim 1, wherein R.sup.1 is a linear alkyl group with 7 to 9 carbon atoms; m is 0; n is a number from >4, and R.sup.4 is a methyl group.

7. The herbicide combination as claimed in claim 1, where component (B) is selected from the group consisting of pyrimidinylsulfonylurea herbicides, amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, methiopyrisulfuron, monosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, trifloxysulfuron, zuomihuanglong, triazinylsulfonylurea herbicides, chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, iofensulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, tritosulfuron and mixtures thereof.

8. The herbicide combination as claimed in claim 1, where component (B) is selected from the group consisting of iodosulfuron-methyl, foramsulfuron, mesosulfuron-methyl, flazasulfuron, amidosulfuron, ethoxysulfuron thiencarbazone-methyl nicosulfuron and mixtures thereof.

9. The herbicide combination as claimed in claim 1, where component (B) is selected from the group consisting of iodosulfuron and nicosulfuron.

10. The herbicide combination as claimed in claim 1, where component (A) is pelargonic acid 6 EO ester methyl ether and component (B) is iodosulfuron.

11. The herbicide combination as claimed claim 1, where component (A) is pelargonic acid 6 EO ester methyl ether and component (B) is nicosulfuron.

12. The herbicide combination as claimed in claim 1, where component (A) is C.sub.8/C.sub.10 fatty acid 6 EO ester methyl ether and component (B) is iodosulfuron.

13. The herbicide combination as claimed in claim 1, where component (A) is pelargonic acid 6 EO ester methyl ether and component (B) is nicosulfuron.

14. A method for controlling unwanted vegetation wherein a herbicide combination comprising an effective amount of components (A) and (B), where (A) is one or more fatty acid derivatives of the formula (I), ##STR00004## wherein R.sup.1 is an alkyl group containing 5 to 17 carbon atoms, which is linear or branched R.sup.2, R.sup.3 are, independently, hydrogen, methyl, ethyl or hydroxymethyl with the proviso that one of R.sup.2 and R.sup.3 is hydrogen and the other is different from hydrogen m, n are numbers from 0 to 17, with the proviso that m+n≥1, and m+n+p<18 where the different monomers can be arranged in statistical order, alternatingly or as a block copolymer: R.sup.4 is hydrogen or an alkyl group containing 1 to 10 carbon atoms, which is linear or branched, and (B) is one or more sulfonyl urea herbicides applied to the unwanted vegetation and/or its habitat.

15. (canceled)

Description

EXAMPLES

[0124] The percentages stated hereinafter are percent by weight (% by weight), unless explicitly stated otherwise.

Example 1: Preparation of the Fatty Acid Derivatives of the Invention

[0125] The compounds according to the invention are listed in Table A. All test substances were liquid, which makes them easy to handle and pourable.

TABLE-US-00001 TABLE A Conversion rate (according Test to acid substance Description R1 R2 R3 m n R4 value) A1 Pelargonic acid C8 H H 0 C Me >85 6 EO ester methyl ether A2 C8/C10 fatty acid C7/C9 H H 0 C Me >85 6 EO ester methyl ether

[0126] General Procedure for the Synthesis of Alcohol Ethoxylate Esters A1 and A2

[0127] Alcohol ethoxylates were synthesized according to standard alkoxylation procedures as described in (e.g. US2012/310004). In a flask, equipped with a Dean-Stark-head, alcohol ethoxylates or glycerol were mixed with the respective carboxylic acid at a stoichiometric mixture, a catalytic amount of sulfuric acid was added and the mixture was heated up to 200° C. upon stirring under a constant stream of nitrogen. Reaction progress was followed by water separation and acid value. The final product was characterized by NMR spectroscopy and titration methods.

Example 2: Results of Greenhouse Trials to Test Herbicidal Activity of Inventive Compounds in Combination with Sulfonylurea Herbicides

[0128] Standard post emergence herbicide application procedures were used, as described below, to apply inventive compounds in combination with sulfonylurea herbicides.

[0129] Seed of monocotyledonous and dicotyledonous harmful plants such as Brassica napus (BRSNW) Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Digitaria Sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Erigeron canadensis (ERICA), Galium aparine (GALAP), Lolium perenne (LOLPE), Sectaria viridis (SETVI), Solanun nigrum (SOLNI), Viola arvensis (VIOAR) were sowed in 18 cm.sup.2 pots. The plants were placed in a greenhouse under controlled environmental conditions, and sub-irrigation. About one week after emergence, seedlings were thinned as needed, including removal of any unhealthy or abnormal plants, to create a uniform series of test pots.

[0130] The plants were maintained for the duration of the test in the greenhouse, where they received a mean of 70 μmol m-2 s-1 of light per day/night. Temperatures averages about 24° C. during the day and about 20° C. during the night. Plants were sub-irrigated throughout the test to ensure adequate soil moisture levels.

[0131] Pots were assigned to different treatment in a randomized experimental design. A set of pots was left untreated as a reference against which effects of the treatments could later be evaluated. Application of tested formulations was made in a spray cabin model 01S-15E designed by CheckTec using the following parameters: [0132] Two edge nozzle Lechler OC2, 200 L/ha, 3 bars. [0133] Two edge nozzle Lechler OC3, 500 L/ha, 3 bars.

[0134] The distance of the nozzle from the plants was between 50 to 53 cm. and the nozzle spacing was 50 cm.

[0135] After treatment, pots were returned to the greenhouse until ready for evaluation. Evaluations were performed at different times after application (DAT: days after treatment), depending on the experiment.

[0136] For evaluation of herbicidal effectiveness, all plants in the test were examined by a single technician, who recorded percent control, a visual measurement of the effectiveness of each treatment by comparison with untreated plants. Control of 0% indicates no effect, and control of 100% indicates that all of the plants are completely dead. The reported % control values represent the average for all replicates of each treatment.

[0137] Iodosulfuron-methyl-sodium and Nicosulfuron were applied as dilutions of the active ingredient in water.

[0138] Generally, the compounds according to the invention displayed particularly similar or better herbicidal activity than the standard products in post-emergence application method against several harmful plants selected from the previous group.

TABLE-US-00002 TABLE 1 Effectiveness control in Solanum nigrum - SOLNI Spray Vol: 500 L/ha Pest Code: SOLNI Treatment-Evaluation Interval N° Treatment Rate Unit 1 DAT 2 DAT 7 DAT 15 DAT 21 DAT 1 A1 0.1 % w/w 0.00 0.00 0.00 0.00 0.00 2 A1 2.5 % w/w 10.00 21.25 13.75 7.75 5.00 3 A1 5 % w/w 26.00 42.50 32.50 28.75 27.50 4 A1 10 % w/w 65.50 75.50 72.50 63.75 53.00 5 A1 0.1 % w/w 0.00 0.00 10.00 25.00 50.00 Iodosulfuron- 10 g Al/ha methyl-sodium 6 A1 2.5 % w/w 3.00 5.00 6.25 13.25 25.00 Iodosulfuron- 10 g Al/ha methyl-sodium 7 A1 5 % w/w 45.00 60.00 73.75 90.75 92.00 Iodosulfuron- 10 g Al/ha methyl-sodium 8 A1 10 % w/w 73.75 78.75 83.00 95.00 95.00 Iodosulfuron- 10 g Al/ha methyl-sodium 9 Iodosulfuron- 10 g Al/ha 0.00 0.000 5.00 25.00 47.50 methyl-sodium

TABLE-US-00003 TABLE 2 Effectiveness control in Solanum nigrum - SOLNI Spray Vol: 200 L/ha Pest Code: SOLNI Treatment-Evaluation Interval N° Treatment Rate Unit 1 DAT 2 DAT 7 DAT 15 DAT 21 DAT 1 A1 0.1 % w/w 0.00 0.00 0.00 0.00 0.00 2 A1 2.5 % w/w 0.00 0.00 0.00 0.00 0.00 3 A1 5 % w/w 0.75 3.50 3.50 0.00 0.00 4 A1 10 % w/w 25.00 48.50 50.50 47.50 38.75 5 A1 0.1 % w/w 0.00 0.00 0.00 8.75 9.25 Iodosulfuron- 10 g Al/ha methyl-sodium 6 A1 2.5 % w/w 0.00 0.00 0.00 10.00 10.00 Iodosulfuron- 10 g Al/ha methyl-sodium 7 A1 5 % w/w 2.25 6.75 6.75 17.00 22.50 Iodosulfuron- 10 g Al/ha methyl-sodium 8 A1 10 % w/w 30.75 48.50 56.00 66.50 66.50 Iodosulfuron- 10 g Al/ha methyl-sodium 9 Iodosulfuron- 10 g Al/ha 0.00 0.00 0.00 12.50 13.75 methyl-sodium

TABLE-US-00004 TABLE 3 Effectiveness control in Sectaria Viridis - SETVI Spray Vol: 200 L/ha Treatment-Evaluation Interval Pest code: SETVI 1 2 7 10 16 22 28 N° Treatment Rate Unit DAT DAT DAT DAT DAT DAT DAT 1 Nicosulfuron 40 g Al/ha 0.00 0.00 5.00 7.00 10.75 7.75 7.00 2 A1 7.5 % w/w 18.50 23.00 30.00 38.00 63.25 63.25 64.00 Nicosulfuron 20 g Al/ha 3 A1 7.5 % w/w 20.00 23.50 35.00 64.50 83.25 83.25 84.50 Nicosulfuron 40 g Al/ha 4 A1 7.5 % w/w 19.25 21.25 21.25 20.00 16.00 16.00 0.00

TABLE-US-00005 TABLE 4 Effectiveness control in Galium aparine - GALAP Spray Vol: 200 L/ha Treatment-Evaluation Interval Pest code: GALAP 1 2 7 10 16 22 28 N° Treatment Rate Unit DAT DAT DAT DAT DAT DAT DAT 1 Nicosulfuron 40 g Al/ha 0.00 0.00 3.00 10.00 12.75 12.75 12.75 2 A1 7.5 % w/w 31.25 33.50 50.00 77.50 82.50 82.50 82.50 Nicosulfuron 20 g Al/ha 3 A1 7.5 % w/w 32.75 33.50 60.00 85.00 88.50 88.50 88.50 Nicosulfuron 40 g Al/ha 4 A1 7.5 % w/w 31.75 34.00 35.75 20.00 10.75 10.75 10.75

TABLE-US-00006 TABLE 5 Effectiveness control in Brassica napus - BRSNW Spray Vol: 200 L/ha Treatment-Evaluation Interval Pest Code: BRSNW 1 2 7 10 16 22 28 N° Treatment Rate Unit DAT DAT DAT DAT DAT DAT DAT 1 Iodosulfuron- 10 g Al/ha 0.00 0.00 6.75 8.50 50.75 99.00 99.00 methyl-sodium 2 A1 7.5 % w/w 77.50 81.00 85.00 86.75 93.75 96.75 96.75 Iodosulfuron- 5 g Al/ha methyl-sodium 3 A1 7.5 % w/w 75.75 78.50 85.00 87.50 90.25 94.50 94.50 Iodosulfuron- 7.5 g Al/ha methyl-sodium 4 A1 7.5 % w/w 76.50 79.00 85.75 88.00 93.00 95.50 95.50 Iodosulfuron- 10 g Al/ha methyl-sodium 5 A1 7.5 % w/w 74.25 78.00 75.00 56.25 39.25 33.50 32.50

TABLE-US-00007 TABLE 6 Effectiveness control in Lolium perenne - LOLPE Spray Vol: 200 L/ha Treatment-Evaluation Interval Pest Code: LOLPE 1 2 7 10 16 22 28 N° Treatment Rate Unit DAT DAT DAT DAT DAT DAT DAT 1 Iodosulfuron- 10 g Al/ha 0.00 0.00 0.00 0.00 0.00 0.00 0.00 methyl-sodium 2 A1 7.5 % w/w 11.50 11.50 11.50 35.50 40.00 68.75 68.75 Iodosulfuron- 5 g Al/ha methyl-sodium 3 A1 7.5 % w/w 12.00 12.00 12.00 46.00 48.00 70.00 73.75 Iodosulfuron- 7.5 g Al/ha methyl-sodium 4 A1 7.5 % w/w 10.00 10.00 10.00 40.75 47.50 72.50 82.75 Iodosulfuron- 10 g Al/ha methyl-sodium 5 A1 7.5 % w/w 11.50 11.50 5.00 0.00 0.00 0.00 0.00