MIXTURES OF PYRIDAZINES AS HERBICIDAL COMPOSITIONS

Abstract

The present invention relates to compositions comprising as component (A) a compound of formula (I) or an agrochemically acceptable salt thereof wherein R.sup.1 is H or methyl; and as component (B) at least one compound, or agrochemically acceptable salt thereof, selected from the group consisting of B-I, B-II, B-III, B-IV, B-V, B-VI, B-VII, B-VIII, B-IX and to their use in controlling plants or inhibiting plant growth.

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Claims

1. A composition comprising as component (A) a compound of formula (I) or an agrochemically acceptable salt thereof: ##STR00008## wherein R.sup.1 is H or methyl; and as component (B) at least one compound, or agrochemically acceptable salt thereof, selected from the group consisting of: ##STR00009## ##STR00010##

2. A composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 0.01:1 to 100:1.

3. A composition according to claim 1 wherein the weight ratio of component (A) to component (B) is from 0.025:1 to 20:1.

4. A composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 1:30 to 16:1.

5. An agrochemical composition comprising a herbicidally effective amount of a composition as defined in claim 1.

6. A composition according to claim 5, further comprising at least one additional active ingredient.

7. A composition according to claim 6, wherein the at least one additional active ingredient comprises at least one additional pesticide.

8. A composition according to claim 7, wherein the additional pesticide is a herbicide or herbicide safener.

9. A composition according to claim 5 additionally comprising an agriculturally-acceptable formulation adjuvant and/or an agrochemically-acceptable diluent or carrier.

10. A method of controlling unwanted plant growth, comprising applying a herbicidally effective amount of a composition as claimed in claim 1 to the unwanted plants, to parts thereof or to the locus thereof.

11. Use of a composition as defined in claim 1 as a herbicide.

12. A formulation comprising a composition according to claim 1, comprising from 0.01 to 90% by weight of active agents, from 0 to 25% of agriculturally acceptable surfactant and from 10 to 99.9% solid or liquid formulation inerts and adjuvant(s).

13. A concentrated composition for dilution by a user, comprising a composition according to claim 1, comprising of from 2 to 80%, preferably between about 5 and 70%, by weight of active agents.

Description

EXAMPLES

Formulation Examples

[0081]

TABLE-US-00003 Wettable powders a) b) c) active ingredients 25%  50% 75% sodium lignosulfonate 5%  5% — sodium lauryl sulphate 3% —  5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62%  27% —

[0082] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

TABLE-US-00004 Powders for dry seed treatment a) b) c) active ingredients 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — 20

[0083] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

TABLE-US-00005 Emulsifiable concentrate active ingredients 10% octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol of ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

[0084] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

TABLE-US-00006 Dusts a) b) c) Active ingredients  5%  6%  4% Talcum 95% — — Kaolin — 94% — mineral filler — — 96%

[0085] Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

TABLE-US-00007 Extruded granules Active ingredients 15% sodium lignosulfonate  2% Carboxymethylcellulose  1% Kaolin 82%

[0086] The combination is 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.

TABLE-US-00008 Coated granules Active ingredients 8% polyethylene glycol (mol. wt. 200) 3% Kaolin 89% 

[0087] The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

TABLE-US-00009 Suspension concentrate active ingredients 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

[0088] The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

TABLE-US-00010 Flowable concentrate for seed treatment active ingredients 40%  propylene glycol 5% copolymer butanol PO/EO 2% Tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution in 0.5%.sup.  water) monoazo-pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2%.sup.  Water 45.3%  

[0089] The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

[0090] Slow Release Capsule Suspension

[0091] 28 Parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

Biological Examples

[0092] Seeds of Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Digitaria sanguinalis (DIGSA), Lolium perenne (LOLPE), Alopecurus myosuroides (ALOMY), Chenopodium album (CHEAL), Ipomoea hederacea (IPOHE), Stellaria media (STEME), Abutilon threophrasti (ABUTH) and Amaranthus retroflexus (AMARE) were sown in standard sterilised soil in pots. After cultivation for 8 days under controlled conditions in a glasshouse (at 24/19° C., day/night; 16 hours light; no humidity control), the plants were sprayed at 500 l/Ha with an aqueous spray solution derived from the formulation of the technical active ingredients in a small amount of acetone and a solvent and emulsifier mixture referred to as IF50 (11.12% Emulsogen EL360 TM+44.44% N-methylpyrrolidone+44.44% Dowanol DPM glycol ether), to create a 50 g/l solution which was then diluted using 0.2% Genapol X080 (CAS Number: 9043-30-5) as diluent to give the desired final dose of test compound.

[0093] Where active ingredients were applied as mixtures, aqueous spray solutions were prepared as above, containing both active ingredients.

[0094] The test plants were then grown under controlled conditions in a glasshouse (at 24/18° C., day/night; 15 hours light; 50% humidity) and watered twice daily. After 13 days, the test was evaluated visually for percentage phytotoxicity to the plants (where 100=total damage to plant; 0=no damage to plant; and NC=not captured) when compared to control untreated plants. Two to four replicates were applied for each treatment in a randomised block test design.

[0095] The results for the individual active ingredients are shown in Table 1 below and the results for combinations of the present invention are shown in Table B2 below.

TABLE-US-00011 TABLE B1 Post-emergence control of weed species of individual compounds Rate Compound (g/ha) SETFA ECHCG DIGSA LOLPE ALOMY IPOHE ABUTH CHEAL AMARE STEME Table B1.1 - Control of weed species by compound A-I A-I 0.625 0 0 0 0 0 13 6 6 14 34 A-I 1.25 0 0 0 0 0 24 5 1 44 64 A-I 2.5 13 8 3 3 0 53 21 13 70 66 A-I 5 43 39 22 28 9 63 58 28 74 79 A-I 10 72 64 35 43 21 74 60 55 73 84 Table B1.2 - Control of weed species by compound B-I B-I 0.625 0 0 0 0 0 53 78 85 63 63 B-I 1.25 5 8 8 10 0 58 80 73 70 65 B-I 2.5 0 0 0 0 0 58 83 83 80 80 B-I 5 0 0 0 0 0 63 90 91 80 85 B-I 10 5 10 0 0 5 75 85 93 93 90 Table B1.3 - Control of weed species by compound B-II B-II 0.625 0 0 0 0 0 5 0 5 0 0 B-II 1.25 3 5 5 5 3 15 40 15 13 10 B-II 2.5 0 0 0 0 0 20 43 30 25 28 B-II 5 5 8 10 5 5 45 58 55 53 53 B-II 10 0 5 3 0 0 55 70 65 58 70 Table B1.4 - Control of weed species by compound B-III B-III 3.125 66 70 72 30 NC 9 10 6 4 13 B-III 6.25 68 70 74 43 NC 11 4 10 6 21 B-III 12.5 70 73 78 55 NC 15 3 14 10 14 B-III 25 74 73 79 70 NC 24 19 44 21 46 B-III 50 73 75 80 75 NC 28 18 56 31 71 Table B1.5 - Control of weed species by compound B-IV B-IV 31.25 0 0 0 0 0 75 15 15 73 68 B-IV 62.5 0 0 0 0 0 35 3 30 80 78 B-IV 125 23 45 18 33 23 88 13 15 83 80 B-IV 250 48 53 38 48 50 89 45 20 85 80 B-IV 500 50 63 70 80 73 93 60 58 83 83 Table B1.6 - Control of weed species by compound B-V B-V 0.08 0 0 0 0 0 23 23 8 35 15 B-V 0.16 0 0 13 5 5 50 75 63 100 45 B-V 0.32 20 10 40 38 50 55 85 78 100 85 B-V 0.625 20 8 50 30 55 93 100 80 100 95 B-V 1.25 33 20 68 60 78 88 100 95 100 100 Table B1.7 - Control of weed species by compound B-VI B-VI 0.625 0 0 0 0 0 25 48 75 83 65 B-VI 1.25 0 0 0 0 0 35 70 80 83 75 B-VI 2.5 5 25 13 5 10 38 78 83 90 90 B-VI 5 2 10 15 5 8 48 80 94 98 93 B-VI 10 40 53 43 25 25 65 93 98 100 99

[0096] To determine if mixtures of active ingredients had a synergistic effect on percentage phytotoxicity of the test plants, Colby's formula was applied: S. R. Colby (1967) “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, p. 22., E=X+Y−(X*Y/100), where [0097] X=average percent phytotoxicity of herbicide A when applied at a certain rate [0098] Y=average percent phytotoxicity using herbicide B when applied at a certain rate [0099] E=the expected effect of the mixture of herbicides A and B as calculated from the Colby formula.

TABLE-US-00012 TABLE B2 Post-emergence herbicidal activity of compounds of the present invention comprising mixtures of components (A) and (B) compared with activity of the individual components. B2.1 - Herbicidal activity of composition 1.001 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.1.1 - SETFA A-I 2.5 13 — — B-I 1.25 5 — — A-I + B-I 2.5 + 1.25 65 17 48 B1.1.2 - ECHCG A-I 2.5 8 — — B-I 1.25 8 — — B-I 5 0 — — A-I + B-I 2.5 + 1.25 41 14 27 A-I + B-I 2.5 + 5   20  8 12 B2.1.3 - DIGSA A-I 2.5 3 — — B-I 1.25 8 — — B-I 2.5 0 — — B-I 5 0 — — A-I + B-I 2.5 + 1.25 68 10 58 A-I + B-I 2.5 + 2.5  13  3 10 A-I + B-I 2.5 + 5   13  3 10 B2.1.4 - LOLPE A-I 2.5 3 — — A-I 5 28 — — B-I 1.25 10 — — B-I 2.5 0 — — B-I 10 0 — — A-I + B-1 2.5 + 1.25 50 12 38 A-I + B-I 2.5 + 2.5  20  3 17 A-I + B-I 5 + 10 40 28 12 B2.1.5 - ALOMY A-I 2.5 0 — — B-I 1.25 0 — — A-I + B-I 2.5 + 1.25 58  0 58 B2.2 - Herbicidal activity of composition 1.006 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.2.1 - SETFA A-I 1.25 0 — — B-VI 1.25 0 — — A-I + B-VI 1.25 + 1.25  10  0 10 B2.2.2 - ECHCG A-I 1.25 0 — — B-VI 0.625 0 — — A-I + B-VI 1.25 + 0.625 10  0 10 B2.2.3 - ALOMY A-I 2.5 0 — — B-VI 5 8 — — A-I + B-VI 2.5 + 5   18  8 10 B2.3 - Herbicidal activity of composition 1.005 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.3.1 - SETFA A-I 1.25 0 — — B-V 0.08 0 — — A-I + B-V 1.25 + 0.08  10  0 10 B2.3.2 - DIGSA A-I 2.5 0 — — A-I 0.625 1 — — B-V 0.16 13 — — B-V 0.08 0 — — A-I + B-V 2.5 + 0.16 28 13 15 A-I + B-V 0.625 + 0.08  15  1 14 B2.3.3 - LOLPE A-I 2.5 1 — — A-I 0.625 0 — — B-V 0.16 5 — — B-V 0.08 0 — — A-I + B-V 2.5 + 0.16 28  6 22 A-I + B-V 0.625 + 0.08  10  0 10 B2.3.4 - ALOMY A-I 2.5 0 — — A-I 5.0 0 — — B-V 0.16 5 — — B-V 0.625 55 — — A-I + B-V 2.5 + 0.16 23  5 18 A-I + B-V  5.0 + 0.625 65 55 10 B2.3.5 - CHEAL A-I 1.25 21 — — A-I 0.625 6 — — B-V 0.08 8 — — A-I + B-V 1.25 + 0.08  40 27 13 A-I + B-V 0.625 + 0.08  43 13 30 B2.4 - Herbicidal activity of composition 1.004 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.4.1 - SETFA A-I 1.25 0 — — A-I 2.5 0 — — B-IV 62.5 0 — — B-IV 125 22 — — A-I + B-IV 1.25 + 62.5  28  0 28 A-I + B-IV 2.5 + 125  33 23 10 B2.4.2 - ECHCG A-I 1.25 0 — — B-IV 62.5 0 — — A-I + B-IV 1.25 + 62.5  18  0 18 B2.4.3 - DIGSA A-I 10 8 — — B-IV 250 38 — — A-I + B-IV 10 + 250 53 42 10 B2.4.4 - LOLPE A-I 2.5 1 — — A-I 5 5 — — A-I 10 35 — — A-I 0.625 0 — — A-I 1.25 0 — — B-IV 62.5 0 — — B-IV 125 33 — — B-IV 250 48 — — B-IV 31.25 0 — — A-I + B-IV 2.5 + 62.5 13  1 12 A-I + B-IV  5 + 125 65 36 29 A-I + B-IV 10 + 250 85 66 19 A-I + B-IV 0.625 + 31.25  25  0 25 A-I + B-IV 1.25 + 62.5  10  0 10 A-I + B-IV  5 + 250 63 50 13 A-I + B-IV 2.5 + 250  68 48 20 B2.4.5 - ALOMY A-I 5 0 — — A-II 0.625 0 — — B-IV 125 23 — — B-IV 31.25 0 — — B-IV 250 50 — — A-I + B-IV  5 + 125 63 23 40 A-I + B-IV 0.625 + 31.25  13  0 13 A-I + B-IV  5 + 250 63 50 13 B2.4.6 - IPOHE A-I 2.5 48 — — A-I 1.25 78 — — B-IV 62.5 35 — — A-I + B-IV 2.5 + 62.5 98 66 32 A-I + B-IV 1.25 + 62.5  98 85 13 B2.4.7 - ABUTH A-I 5 55 — — A-I 1.25 26 — — B-IV 125 13 — — A-I + B-IV  5 + 125 73 63 10 A-I + B-IV 1.25 + 125   50 36 14 B2.4.8 - CHEAL A-I 5 26 — — A-I 10 15 — — A-I 2.5 16 — — B-IV 125 15 — — B-IV 250 20 A-I + B-IV  5 + 125 50 37 13 A-I + B-IV 10 + 250 73 32 41 A-I + B-IV 2.5 + 250  53 33 20 B2.5 - Herbicidal activity of composition 1.003 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.5.1 - LOLPE A-I 1.25 3 — — A-I 0.625 3 — — B-III 6.25 43 — — B-III 12.5 55 — — A-I + B-III 1.25 + 6.25  60 44 16 A-I + B-III 0.625 + 12.5  68 56 12 B2.5.2 - STEME A-I 1.25 58 — — B-III 12.5 14 — — A-I + B-III 1.25 + 12.5  80 63 17 B2.5.3 - CHEAL A-I 1.25 13 — — B-III 12.5 14 — — A-I + B-III 1.25 + 12.5  43 25 18 B2.6 - Herbicidal activity of composition 1.002 of Table 1 Compound Rate (g/ha) Observed Expected Difference B2.6.1 - ECHCG A-I 2.5 8 — — A-I 5 39 — — B-II 5 8 — — B-II 10 5 — — A-I + B-II 2.5 + 5   25 14 11 A-I + B-II 5 + 10 53 42 11 B2.6.2 - DIGSA A-I 5 21 — — A-I 2.5 3 — — A-I 1.25 0 — — B-II 2.5 0 — — B-II 5 10 — — B-II 10 3 — — A-I + B-II  5 + 2.5 38 21 17 A-I + B-II 2.5 + 2.5  20  3 17 A-I + B-II 5 + 5  43 29 14 A-I + B-II 1.25 + 2.5  10  0 10 A-I + B-II 2.5 + 5   33 12 21 A-I + B-II 5 + 10 53 23 30 B2.6.3 - LOLPE A-I 2.5 3 — — A-I 5 28 — — B-II 2.5 0 — — B-II 5 5 — — B-II 10 0 — — A-I + B-II 2.5 + 2.5  15  3 12 A-I + B-II 2.5 + 5   18  7 11 A-I + B-II 5 + 10 38 28 10 B2.6.4 - ABUTH A-I 1.25 5 — — A-I 2.5 21 — — A-I 0.625 6 — — B-II 0.625 0 — — B-II 1.25 40 — — B-II 2.5 43 — — A-I + B-II 1.25 + 0.625 38  5 33 A-I + B-II 2.5 + 1.25 65 53 12 A-I + B-II 0.625 + 0.625  28  6 22 A-I + B-II 2.5 + 2.5  70 55 15 B2.6.5 - CHEAL A-I 2.5 13 — — A-I 1.25 1 — — B-II 1.25 15 — — B-II 2.5 30 — — A-I + B-II 2.5 + 1.25 53 26 27 A-I + B-II 2.5 + 2.5  53 39 14 A-I + B-II 1.25 + 2.5  43 31 12 B2.6.6 - AMARE A-I 1.25 44 — — B-II 0.625 0 — — B-II 1.25 13 — — B-II 2.5 25 — — A-I + B-II 1.25 + 0.625 60 44 16 A-I + B-II 1.25 + 1.25  63 51 12 A-I + B-II 1.25 + 2.5  73 58 15 B2.6.7 - STEME A-I 1.25 64 — — A-I 2.5 66 — — A-I 0.625 34 — — B-II 0.625 0 — — B-II 1.25 10 — — A-I + B-II 1.25 + 0.625 75 64 11 A-I + B-II 2.5 + 1.25 89 70 19 A-I + B-II 0.625 + 0.625  55 34 21 A-I + B-II 1.25 + 1.25  78 67 11