MXPA97004152A

MXPA97004152A - New compositions herbici

Info

Publication number: MXPA97004152A
Application number: MXPA/A/1997/004152A
Authority: MX
Inventors: Millet Jeanclaude; Rolfdeege
Original assignee: Bayer Aktiengesellschaft; Rhonepoulenc Agrochimie
Priority date: 1994-12-09
Filing date: 1997-06-05
Publication date: 1998-07-03

Abstract

The present invention relates to a method for controlling the growth of herbs in a site, characterized in that it comprises the application to said site of a herbicidically effective amount of: a) a 4-benzoylisoxazole of formula (I): wherein R is hydrogen CO2R3, R1 is cyclopropyl, R2 is selected from halogen, -S (O) pMe and trifluoromethyl, n is two, p is zero, and R3 is C1-4 alkyl, and b) N-isopropyl- (5-) trifluoromethyl-1,3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide) having the formula (I

Description

NEW HERBICIDAL COMPOSITIONS FIELD OF THE INVENTION This invention relates to new compositions comprising an N-isopropylheteroaryloxyacetanilide herbicide and a 4-benzoylisoxazole derivative, and their use as herbicides.

BACKGROUND OF THE INVENTION The compounds of the invention are known in the art. N-Isopropylheteroaryloxyacetanilides are described in European Patent Publication Number 0348737, published January 3, 1990, which in particular discloses N-isopropyl- (5-trifluoromethyl-1,3,4-thiadiazole). -2-i1) - (4'-fluoro-oxyacetanyl-lide) as compound 34. The 4-Benzoylisoxazoles are described in, for example, European Patent Publication Numbers 0418175, 0487357, 0527036 and 0560482. In particular, the Publication of European Patent Number 0560482, published on February 10, 1993, discloses 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethylbenzoyl) isoxaxol. Any of these publications show that these compounds possess herbicidal activity. Thus, none of the publications show specific anti-gram properties in the compounds. Patent EP-A1-0527036 shows that the acetanilide compounds can REF: 24772 be applied from 0.01 to 10 Kg of active compound per hectare of surface earth, preferably from 0.05 to 5 Kg per-hectare; there are no precise details of the doses that are used for the application of the compounds to treat grasses. Patent EP-A1-0527036 shows that the compounds of the invention possess great activity in comparison with compounds known against certain herbal species. Here, the literature does not show mixtures of these compounds; this does not suggest that such a mixture is expected to be particularly useful as an anti-graminicide. So far, the mixture most commonly used in this area of herbal science, comprises metolachlor and atrazine. These are often recommended for use at doses of around 1 to 2.5 Kg per hectare of metolachlor and around 0.5 to 2.5 Kg per-hectare atrazine. An object of the invention is, in this way, to provide a suitable mixture as a graminicide, which can be used at reduced doses of active compound in comparison with the known products. Notably, it has been found that the mixture of N-isopro-pilo- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetinalide) with the derivatives of -benzolisoxazole, provides an effective control of an extremely broad range of both monocotyledonous and dicotyledonous hens at reduced doses, when compared to those known compounds. Moreover, this mixture provides effective control along with selectivity in important crop species, such as corn. Surprisingly, and in addition to this, it has been found that under certain conditions, the combined herbicidal activity of certain 4-benzoylisoxazoles with N-isopropyl- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide) for the control of certain herbal species eg Setaria viridis, Echinochloa crus-galli, Amaranthus retroflexus and Poligonum lapathifolium, is larger than expected, without an unacceptable increase in crop phytotoxicity, i.e. the mixture has a lot of synergism as defined by Limpel, L.E., P.H. Schuldt and D. Lamont, 1962, 1. Proc. NE CC 16, 48-53, also known -such as Colby's formula (Colby SR, 1967, Weeds 15, 20-22), using the formula: E = X + Y - XY / 100 where E = percent inhibition expected in growth by a mixture of two herbicides A and B at defined doses. X =? A hundred percent growth inhibition by herbicide A at a defined dose. Y = percent growth inhibition by herbicide B at a defined dose. When the observed percentage of inhibition by the mixture is larger than the expected value of E, using the above formula, the combination is synergistic.

This remarkable synergistic effect provides quality in the control of those competitive herbs of many crop species, and contributes to a considerable reduction in the amount of active ingredient that is required for the control -herbal.

DESCRIPTION OF THE INVENTION According to the present invention, it provides a method for controlling the growth of herbs at a site, which comprises applying to said site a herbicidically effective amount of: (a) a 4-benzoylisoxazole of formula (I) : where 3 R is hydrogen or -C0? R; R is cyclopropyl; 2 R is selected from halogen, -S (0) Me and trifluoromethyl, n is two or three; p is zero, one or two; Y 3 R is C alkyl; (b) N-isopropyl-SS-trifluoromethyl-l.S ^ -thiadiazole ^ -yl) ^ - ^ -fluoro-oxyacetanilide) having the formula (II) (H) Preferably the 4-benzoylisoxazole derivative of formula (I) is 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethyl) -benzoylisozaxol, hereinafter referred to as Compound A. For convenience, N-isopropyl- (5- trifluoromethyl-1, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide) hereinafter will be referred to as Compound B. The amounts that apply of 4-benzoylisoxazole and of compound B, vary depending on the the herbs present and their population, the compositions used, the time of application, the climatic and pedological conditions, and (when they are used to control the growth of herbs in harvest areas) the crop to be treated. In general, taking these factors into account, the application rates of 5 to 500 g of 4-benzoylisoxazole and of 10 to 10,000 g of compound B per-hectare give good results. So, it will be understood that higher or lower application rates can be used, depending on the problem of herbal control found. The method of the invention is most preferably used for herbal control at a used site, or is used for the growth of a crop. When applied to a crop growth area, the application rate will be - enough to control the growth of herbs without causing substantial permanent damage to the crop. Crops where the mixture can be used include soybeans, sugarcane, cotton, corn, sunflower, peas, potatoes, garbar. or, sorghum rice and cereals. The preferred crop, in terms of the selectivity of the mixture, is corn. For the selective control of herbs in a site of herbal infestation which is an area used, or to be used, for the application of crop growth, proportions of about 5 to 200 g of 4-benzoylisoxazole and about 50 to 5,000 g of compound B per hectare are particularly suitable, preferably from about 50 to 130 g of 4-benzoylisoxazole and about 80 to 875 g of compound B per hectare, more preferably from 75 to 100 g ( about 80 g are more preferred) of 4-benzoylisoxazole and 300 to 500 g (about 360 g are more preferred under humid conditions and about 450 g under drier conditions) of compound B per hectare. The mixture is preferably applied pre-emergence, but can also be applied post-emergence (especially at an early stage of herbal growth). By the term "pre-emergency application" is meant the application to the land in which the seeds of the herbs or seedlings are present before the emergence of the harvest. An example of a pre-emergency application is known as "incorporated into the pre-plant" (PPI), where the herbicide is incorporated into the soil prior to the planting of the crop. Early application (PPI) can also be used. The mixture can also be applied by pre-planting (i.e. before the crop is planted) either to the surface of the soil or incorporated into the soil. Treating early pre-planting using the mixture (particularly applied to the surface) are also a feature of the method of the invention. According to another feature of the present invention, it provides herbicidal compositions comprising: (a) a 4-benzoylisoxazole derivative of formula I as defined above; and (b) N-isopropyl- (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl) -4- (4 ' -fluoro-oxyacetanilide); in association with, and preferably homogeneously dispersed in, a herbicidically acceptable diluent or carrier, and / or an active agent surface. The term "herbicidal composition" is used in a broad sense to include not only compositions which are available for use as herbicides, but also concentrates which can be diluted before use. Preferably, the compositions contain from 0.05 to 90% by weight of 4-benzoylisoxazole and compound B.

Unless otherwise indicated, the percentages and -proportions will appear in this specification in relation to -weight. Generally a composition in which the ratio of (a): (b) is from about 1: 2000 to 50: 1 weight / weight is used, proportions of about 1: 1000 to 4: 1 weight / weight are preferred, ratios of about 1: 17.5 to 1.63: 1 weight / weight are more preferred, and ratios of about 1: 6.67 to 1: 3 weight / weight are especially preferred (ratios of about 1: 4.5 in wet conditions and around of 1: 5.6 in dry conditions, are more preferred). The preferred formulation according to the invention is in the form of a water dispersible granule, although it will be understood that other types of formulations known in the art may also be used. According to the usual practice, a mixing tank can be prepared before being used to combine formulations separated from the individual herbicidal components. According to another feature of the present invention, it provides a product comprising: (a) 4-benxoylisozaxol of formula I as defined above; and (b) N-isopropyl- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide), as a combined preparation for simultaneous, separate or sequential use in the control of the growth of - - herbs in a site. The following non-limiting experiments illustrate the pre-invention. 5 EXPERIMENT Al The following experiments were carried out by Com "" "station A and Compound B, in several fields of research 10 in Europe during the month of May, Compound A (as - a formulation of 750 g / Kg of dispersible granule in water. ) and Compound B (as a 600 g / Kg formulation of water dispersible granule) were tested at the following doses (note that from now on, ai will mean active ingredient): Compound A: 50, 75 , 100, 125 g ai / ha Compound B: 240, 360, 480, 600 g ai / ha Compound A + Compound B: 50 + 240/360/480 g ai / ha 75 + 240/360/480 g ai / ha 20 100 + 240/360/480 g ai / ha The test and application conditions are given in Table 1 (in the Tables that follow, DAT means days after the treatment): TABLE 1 LOCATION Chazay Alzonne Bologna D'azergues France Italy France Texture of Mulch to Earth% Organic Matter 1.8 1.4 1.82 pH 6.9 7.9 8.13% Sand 38 34 34% Clay 41 39 46% Clay 17 22 29 Precipitation mm 25/19 37/55 24/146 15/30 DAT Temperature 13 ° C 18 ° C 19 ° C (when applied) Dry Dry Soil The herbs were planted on the same day as corn. All tests were sprayed from pre-emergence corn as well as planted on the same day or within 2 days after. The conditions of the earth were hot and humid, so the harvest and the herbs emerged and grew rapidly. The precipitation or irrigation occurred within 15 days of application. The results are expressed as a percentage of the phytotoxicity, as shown in Table 2. In this Table, "Obs" is the observed value, the value in parentheses (Exp) is the expected value calculated by the formula of Colby.

RESULTS Colby's formula can be applied to the above data and indicate that in 29 cases, a better level than expected -in herbal control is observed (ie a synergistic interaction), in 2 cases a lower level of activity of the The expected value is observed (ie antagonism) and in 14 cases the -value observed was within 3% of the expected value (ie an additive effect). This clearly shows that in these tests, the vast majority of the results were synergistic.

EXPERIMENT A2 The following experiments were carried out by Compound A and Compound B in several research fields in the United States. Compound A (as a formulation of 750 g / Kg of water-dispersible granule) and Compound B (as a 600 g / Kg formulation of water-dispersible granule) were tested at the following doses: Compound B + Compound A : 240 + 75/100/125 g ai / h 360 + 75/100/125 g ai / ha 480 + 75/100/125 g ai / ha Compound A: 75/100/125/150 g ai / ha Compound B: 240/360/480/600 g ai / ha A commercial standard was also applied, which included metolachlor and atrazine at 1120/1120 g ai / ha and 2240/2240 g - ai / ha of metolachlor / atrazine. The tests were conducted in South Dakota (1 test), Nebraska (1), Iowa (1), Indiana (1), Pennsylvania (1) and Mississippi (1). The species -herbarias were sown in all the locations. All the tests were sprayed in May / June on the same day or within 3 days of planting the corn. In all-tests, rainfall or significant irrigations occurred shortly after spraying and for the next 2 or 3 weeks. The conditions of the test and application field were as shown in Table 3.

TABLE 3 I heard The average results of the tests as a percentage of reduction in the growth of the species to several stages after the treatment, are presented in Tables 4 to 6. Note that in the Tables, the herbal species are represented by the following codes from Bayer and that ATR means Atrazine and MET means metolachlor.

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It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, the content of the following is claimed as property.

Claims

REIVINDICACIOWES

1. A method for controlling the growth of herbs - at a site, characterized in that it comprises the application to said site of a herbicidically effective amount of: (a) a 4-benzoylisoxazole of formula (I): (i) where 3 R is hydrogen or -C0_R; R is cyclopropyl; 2 R is selected from halogen, -S (0) Me and trifluoromethyl, n is two or three; p is zero, one or two; and 3 R is c-t_? I rent; and (b) N-isopropyl- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4 ' -fluoro-oxyacetanilide) having the formula (II):

2. The method according to claim 1, characterized in that the 4-benzoylisoxazole derivative of formula I is 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethyl) benzoylisozaxol

3. The method according to claim 1 or 2, characterized in that an application ratio of about 5 to 500 g per hectare of 4-benzoylisoxazole and about 10 to 10,000 g per hectare of N-isopropyl- (5-trifluoromethyl) is used. -l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide).

4. The method according to claims 1, 2 or 3, characterized in that the site is used, or will be used, for the growth of a crop.

5. The method according to claim 4, characterized in that the harvest is corn.

6. The method according to any one of the preceding claims, characterized in that an application portion of about 5 to 200 g per hectare of 4-benzoylisoxazole and about 50 to 5,000 g per hectare of N-isopropyl- is used. (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide).

7. The method according to any one of the preceding claims, characterized in that an application ratio of about 50 to 130 g per hectare of 4-benzoylisoxazole and about 80 to 875 g per hectare of N-isopropyl- is used. (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide).

8. The method according to any one of the preceding claims, characterized in that an application ratio of about 75 to 100 g per hectare of 4-benzoylisoxazole and about 300 to 500 g per hectare of N-isopropyl- is used. (5-trifluoromethyl-1, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide).

9. The method according to any of the preceding claims, characterized by its application of -pre-emergence.

10. A herbicidal composition characterized by: (a) a 4-benzoylisoxazole derivative of formula I as defined in claim 1; and (b) N-isopropyl- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide); in association with a herbicidally acceptable diluent or carrier, and / or a surface active agent.

11. The composition according to claim 10, characterized in that the 4-benzoylisoxazole derivative of formorm I is 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethyl) benzo-ilisozaxol.

12. The composition according to claim 10 or 11, characterized in that the weight ratio of (a): (b) is from about 1: 2000 to 50: 1.

13. The composition according to claim 10 or 11, characterized in that the weight ratio of (a): (b) is from about 1: 1000 to 4: 1.

14. The composition according to claim 10 or 11, characterized in that the weight ratio of (a): (b) is from about 1: 17.5 to 1.63: 1.

15. The composition according to claim 10 or 11, characterized in that the weight ratio of (a) : (b) is around 1: 6.67 to 1: 3.

16. The composition according to any of claims 10 to 15, characterized in that it is in the form of a granule dispersible in water.

17. A product characterized by a herbicidally effective amount of: (a) a 4-benzoylisozaxol of formula I as defined in claim 1; and (b) N-isopropyl- (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl) -4- (4'-fluoro-oxyacetanilide); as a combined preparation for simultaneous, separate or sequential use for control on the growth of herbs at a site.