HU193214B - Synergic herbicide compositions for extirpating panicum miliaceum containing chloro-acetamide derivatives and substituted benzene derivatives as active agents - Google Patents

Abstract

The invention relates to herbicidal compositions having a content of 1-90 wt .-% of an active ingredient combination of N- (2-ethyl-6-methyl-phenyl) -N-ethoxy-methyl-2-chloroacetamide and 2-nitro-1 - (4-nitro-phenoxy) -4-trifluoromethylbenzene having a weight ratio of 1: 4 to 2.3: 1. In addition, the agents having a synergistic effect contain conventional auxiliaries and tracer substances. The funds allow effective control of monocotyledonous weeds such as Panicum miliaceum in maize crops. DD # AP

Description

SUMMARY OF THE INVENTION The present invention relates to a herbicidal composition having a synergistic effect, comprising as active ingredient 1-90% by weight of N- (dialkylphenyl) -N- / alkoxy-α-yl / -2-chloroacetamidothachol of the structure (I). an alkoxyalkyl group in which the alkoxy and alkyl groups may be C 1 -C 4, R ₂ and R ₃ are the same or different C 1 -C 4 alkyl groups - and 2-nitro-1/4 -nitrophenoxy-4- (trifluoromethyl) -benzene (FLUORODIFEN) in a weight ratio (1: 4) to (2.3: 1). The formulations contain the usual liquid or solid excipients of the pesticides, as well as excipients and other additives, and are preferably formulated as emulsifiable concentrates, sprayable powders or granules. The synergistic compositions of the present invention are used for preemergent treatment in maize cultures, in particular to control Panicum miliaceum.

The active ingredients of the compositions according to the invention are known per se. For example, the preparation of N- (diacylphenyl) -N- (alkoxyalkyl) -2-chloroacetamides of general formula (I) is described in U.S. Patent No. 3,442,945, and in U.S. Patent No. 1,033,163 for FLUORODIFEN. deals. However, the combined use and synergistic coexistence of the two active ingredients is still unknown. Furthermore, the use of FLUORODIFEN in maize for weed control is unknown.

So far, the most widely used chemical herbicide for maize is the active ingredient chloroaminotriazine. They have the disadvantage that they are ineffective against certain monocotyledonous weeds, as weeds, like maize, are capable of detoxifying these herbicides. Jensen, K.I.N-Stephenson, G.R. - Hunt., L.A .: "Detoxification of atrazine in three Gramineae subfamilies." c. / Weed Sci./ Champaign, III. 1977 Feb.212-22o.p./

It is known that Panicum miliaceum is most able to inactivate the atrazine herbicide after maize and this is the reason why this weed species is currently very widespread. Other herbicides / thiocarbamates, urea derivatives, acetanilides, etc. used in maize are not sufficiently effective against Panicum miliaceum.

Researchers have worked extensively on formulations and biological treatments to control the dangerous weed species, but promising results so far have been limited to post-emergence treatment.

It is therefore an object of the present invention to provide compositions that can effectively control Panicum miliaceum using preemergent weed control technology in corn culture without damaging the crop. To this end, a number of compounds were investigated, including those which were previously unknown in 9 maize weed control. Surprisingly, it has been found that the active ingredients of the compositions of the invention, when used in combination, exhibit synergistic additive effects at some ratios. Effect studies using methods well-suited to biological research / Bánki, L .: Bioassay of pesticides in the laboratory. Akadémiai Kiadó, Budapest 1978. pp. 292-302: Horsfall; J.G./1945/: Fungicides and thier action. Walthem, Mass .; USA, Chronica Botanica .; Scardari, A./1962/: Sinergismo di efficacia anticritlogamica tra Maneb e zolfo o polisolfur) di bario o Thiram. Nitoz Malatt. Plante 61, 3 35, 37-48., 53-69 /. performed.

These methods are particularly suitable for determining the synergistic, additive, or antagonistic effects of two bioactive substances r.i.

The formulations of the present invention comprise, in addition to the customary carriers, excipients and additives for pesticides, in an amount of from 1 to 90% by weight of N- / diazylphenyl / -N- / alkoxyalkyl--2- having the structure: chloroacetamide - where R 1, R ₂ and R ₃ are as defined above - and 2-nitro-1- (4-nitro-phenoxy) -4- (trifluoromethyl) -benzene (FLUORDIFEN) (1: 4) to (2.3: 1) relative to each other. The formulations contain from 1 to 95% by weight, as a liquid and / or solid carrier, of aliphatic and / or aromatic hydrocarbons and / or alcohols and / or ketones and / or esters and / or natural minerals and / or artificial silicates.

As excipients and other additives, the compositions further comprise from 2% to 15% by weight of non-ionic and / or anionic surfactants and / or lignin sulfonic acid derivatives and / or adhesives and / or selectives and / or adhesives with a wetting and / or dispersing action. . The compositions are preferably in the form of water-emulsifiable concentrates for women, sprayable powders or granules.

The emulsifiable concentrate and sprayable compositions of the present invention are used, after dilution with water, and the granular composition is applied directly to the soil as a pre-emulsion to control Pan cum miliaceum weeds grown in maize culture. The optimum rate of application of test pot ^- circumstances approx. 1 kg total active substance / ha.

In particular, the efficacy of N- (2'-ethyl-6'-methylphenyl) -N- (ethoxymethyl) -2-chloroacetamide (ACETO chloro) and FLUORODIFEN as mixtures of different ratios of the active compounds was determined. The separately measured, expected and combined efficacy of the active substances acetochlor (A) and fluorodifen (F) against Panicum miliaceum are shown in Figure 1. Figure 1 shows that at optimal drug ratios, the measured efficacy is more than 30% higher than expected.

This fact clearly demonstrates the synergistic additional effect.

In the following we have extended our synergistic studies to other major N-dialkyl phenyl-N- (alkoxyalkyl) -2-chloroacetamides. N- (2'6'-diethylphenyl) -N- (methoxymethyl) -2-chloroacetamide (ALCHLOR), N- (2,6'-dimethylphenyl) -N- (methoxyethyl) were determined. (-2-chloroacetamide / DIMETACHLOR) and N- (2'-methyl-6'-ethylphenyl) -N- (methoxy-1-methylethyl) -2-chloroacetamide / METOLachlor (active ingredient Panicum) and milodium, even in their various proportions.

Studies have shown that any N- (dialkylphenyl) -N- (alkoxyalkyl) -2-chloroacetamide of formula (1) is also mixed with fluorodifen in a weight ratio of (1: 4) to (2.3: 1). As in Figure 1, there is a significant synergistic effect of more than 30% at optimal ratios. Thus, when used in combination with any one of the compounds of formula (1) and fluorodifen, a synergistic effect is obtained, i.e., N- (dialkylphenyl) -N- (alkoxyalkyl) -2-chloroacetamides may be substituted in their mixtures with fluorodifen.

The novel formulations of the present invention have the advantage that their use enables high efficiency and safe preemergent control of Panicum milaceousum in maize culture, with a relatively low pesticide dose, without the slightest damage to the crop.

The formulations of the present invention and their biological activity are illustrated by the following examples, without limiting the scope of the invention to the embodiments.

Example 1

Breeding pot, greenhouse efficacy studies In a culture pot of cm x 30 cm x 30 cm, 9 kg of a mixture of field and sand soil in a 1: 1 ratio was placed and then placed in the soil.

1θ at 4 cm depth for 100-100 MVSC 1295 / FAO 200 / maize hybrids and 100-100 pc for 2 cm depth. Panicum miliaceum weed seeds were sown. Two sets of experiments were carried out in which the soil surface was treated with an emulsion spray prepared by dilution with an emulsifiable concentrate containing 40% by weight of the active ingredient in Table 1 / EC. The first series of experiments the dose values and the results of the effectiveness testing of the second ²⁰ gi-fourth Tables 5 through 6, control plants not treated with the herbicide s. The soil in each dish were watered ^{from 25,200 to 200} ml of water per day in the experiment, the greenhouse temperature was maintained between 15-25 ° C and light intensity of 24 klux. radiation intensification 70 Wnf ² , 80% reactive humidity.

The experiment was evaluated 15 days after emergence.

The following scale of credit was used to indicate the condition of the plants:

³⁵ 0 = no damage = up to 25% leaf damage = "50% leaf damage or inhibition of growth ^{3 ="} 75% of the leaves increases and the distortion ^U = total growth by inhibition, 10G% death. spreadsheet

Component Name: 2 3 Together 4 bet 5 e 1 6 (c%) 7 8 9 10 11 N, (alkyl) phenyl) -N-falkoxyalkyl chloroacetamide (100% 40 4 8 12 16 20 24 28 32 36 purity) Fluorodifen (100 µg purity 36 32 28 24 20 16 12 8 4 Surfactant: Calcium Dodeci 1 Benzene Born Phonate and Ethoxylated Fat s 8 8 8 8 8 8 8 8 8 8 alcohol mixture / ATLOX 4853 Surfactant: Calcium dodecyl benzosulfonate and nonylphenol polyglycolol ether 2 2 2 2 2 2 2 2 2 2 2 mixture effectATLüX 4831) Selectivity enhancing additive: N- (dichloroacetyl) -1-οχο-4-azas- 4 0th 0.8 1.2 First 6 2.0 2.4 2.8 3.2 3.6 Pyrobicyclo-4,5-decane Cyclohexanone solvent 30 30 30 30 30 30 30 30 30 30 30 Xylene solvent add. 100 100 100 100 100 100 woman 100 100 100 100

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Table 2

ACETOCLOR Test for potency against panicum miliaceum

Acetochlor Chlorine Panicum miliaceum damage dose kg / ha grade (from 100 plants, pcs)

Damage Corn Damage Damage Total Grade% (100 plants, pcs) Total%.

0 1 2 3 4 0 1 2 0.2 35 20 18 12 38.0 100 0 0 0 0.4 27 24 20 14 41.5 95 5 0 1:25 0.6 2, 28 18 16 17 45.0 92 8 0 2.0 0.8 2 28 22 24 24 60.0 90 10 0 2.5 1.0 0 10 24 34 32 72.0 84 12 4 5.0 1.2 0 0 24 36 40 79.C 82 12 6 6.0 1.4 0 0 8 32 60 88.C 70 24 6 9.0 1.6 0 0 0 8 92 98. C 56 28 16 15.0 Kontrol 100 0 0 0 0 0 100 0 0 0 Table 3 FLUOROSIFEN I Efficacy against Panicum miliaceum in pot culture examination fluorodiphen Panicum miliaceum damage Damage Corn damage main ~ Damage dose kg / ha degree (Out of 100 plants, db) altogether % dum Of X100 plants) altogether % 0 1 2 3 4 0 1 2 0.2 16 60 24 0 0 27.0 100 0 0 0 0.4 2 64 34 0 0 l 33.0 100 0 0 0 0.6 0 32 52 1b 0 I 46.0 100 0 0 0 0.8 0 16 60 28 0 I 55.0 100 0 0 0 1 .0 0 0 48 52 C I 63.0 100 0 0 0 1.2 0 0 22 68 1C1 72.0 100 0 0 0 1.4 0 0 8 76 16 , 77.0 95 5 0 1:25 1.6 0 0 0 60 4C I 85.0 90 10 0 2.5 Kontrol 100 0 0 0 0 0 100 0 0 0

The table

ACETOCLOR + FLUORODIFEN Testing for breeding efficacy against Panicum miliaceum

Acetochlor + Flurodifen dose kg / ha Degree of damage to Panicum miliaceum Percentage of damage Corn damage main- Damage to ÖSS2. 7c 0 (Out of 100 plants, 1 2 db) dum 0 (100 1 of plants (db) 2 3 4 0.1 + 0.9 0 0 20 68 12 73.0 100 0 0 0 0.2 0.8 + 0 0 0 68 32 83.0 100 0 0 0 0.3 0.7 + 0 0 0 12 88 97.0 100 0 0 0 0.4 0.6 + 0 0 0 0 100 100.0 95 5 0 1 .25 0.5 0.5 + 0 0 0 0 100 100.0 95 5 0 1:25 0.6 0.4 + 0 0 0 24 76 94.0 92 8 0 2.0 0.7 0.3 + 0 0 24 36 40 79.0 92 8 0 2.0 0.8 0.2 + 0 0 30 40 30 75.0 90 10 0 2.5 0.9 + 0.1 0 0 25 36 29 68.5 88 12 0 3.0 Kontrol 100 0 0 0 0 0 100 0 0 0

The first series of experiments / see. 2nd-4th Tables / results clearly showed that acetochlorochlorofluorodiphene blends in the dose range of /0.2 50 + 0.8 / kg / ha to /0.7+0.3 / kg / ha, i.e. in a weight ratio of 1: 4-2.3: 1, but especially At a weight ratio of 1: 2 to 1: 1, the active ingredient has a significant synergistic effect. Therefore, in our second set of experiments, only such weight ratios were tested. Our results are shown in Tables 5 and 6.

Table 5

Test for potency against ACETOCLOR (A), ALACHLOR (B), DIMETACHLOR (C), METOLACLOR (D) and FLUORODIFEN (F) in Panicum miliaceum

Ingredient Dose Panicum miliaceum Karojba ^c l ^e (kg / ha) linking in stage (plant 100, db)

0 1 2 3 0.2 73 10 6 6 THE 0.7 27 22 21 16 1.0 1 30 24 22 0.2 70 11 8 5 B 0.7 25 24 20 16 1.0 0 28 23 26 0.2 76 8 7 4

4 Damage Corn damage Damage altogether % sum. % grade (out of 100 plants, pcs) 0 1 2 5 15.0 100 0 0 0 14 42.0 92 8 0 2.0 23 59.0 84 4 2 4.5 6 16.5 100 0 0 0 15 43.0 93 7 0 1.75 23 61.0 82 12 4 5.0 5 13.5 100 0 0 0

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Table 5

Test for potency against ACETOCLUR (A), FORMICOR (B), DIMETACLUR (C), METOLACHL (D) and FLUORODIFEN (F) Panicum miliaceum

agent sign: Dose (Kg / ha) Panicum miliaceum damage Károsocás sum. % Corn damage! Damage altogether 7 degree of finishing ( _t 100 prescriptions) woman- grade from bol, db) 0 (100 1 plant- 2 3 4 0 1 2 c 0.7 29 27 16 13 15 39.5 96 4 0 1.0 1.0 6 29 23 23 9 55.0 86 12 2 4.0 0.2 73 1 1 6 5 5 14.5 100 0 0 0 D 0.7 31 21 17 15 16 41.0 90 10 0 2.0 1.0 2 27 22 25 24 60.5 84 13 3 4.75 0.3 44 42 14 0 0 17.5 00 0 0 0 F 0.8 0 36 52 12 0 44.0 100 0 0 0 1.0 0 0 48 50 2 63.5 100 0 0 0 Kontrol - 100 0 0 0 0 0 100 0 0 0

Table 6

Test for potency against Panicum miliaceum in mixtures of acetachlor (A), alachlor (B), dimethachlor (C) and metolachlor (D) with FLUORODIFEN

agent mix sign Dose (Kg / ha) Panicum miliaceum damage! degree (100 women- Damage sum. % Corn damage! damage: altogether X grade bol, db) 0 (100 1 plant- 2 prescription 0 1 , db) 2 3 4 0.2 0.8 + 0 0 6 66 28 80.5 100 0 0 0 0.4 0.6 + 0 0 0 0 100 , 00.0 IOO 0 0 0 A & D 0.6 0.4 + 0 0 0 18 82 95.5 94 6 0 1.75 0.7 0.3 + 0 0 39 40 21 70.5 82 13 5 5.75 0.2 0.8 + 0 0 0 72 28 82.0 100 0 0 0 0.4 0.6 + 0 0 0 0 100 100.0 100 0 0 0 B + D 0.6 0.4 + 0 0 0 0 00 100.0 96 4 0 1.0 0.7 0.3 + 0 0 33 44 23 72.5 83 14 3 5.0 0.2 0.8 + 0 0 13 68 19 76.5 100 0 0 0 C & D 0.4 0.6 + 0 0 0 8 92 98.0 100 0 0 0 0.6 0.4 + 0 0 0 66 34 83.5 97 3 0 0.75 0.7 0.3 + 0 0 36 42 22 71.5 89 9 2 3.25 0.2 0.8 + 0 0 0 70 30 82.5 00 0 0 tt 0.4 0.6 + 0 0 0 0 100 100.0 100 0 0 0 D + F 0.6 0.4 + 0 0 0 40 60 90.0 93 7 0 1.75 0.7 0.3 + 0 0 42 42 16 68.5 85 1 1 4 4.75 Kontrol - 100 0 0 0 0 0 100 0 0 0

Results of the second set of experiments /ld.5.-6. Table 1 / shows a high degree of synergistic effect as in the first. The efficacy of each mixture depends on the active compound ratios used and is independent of the quality of N- (dialkyl) 1-phenyl / N- (alkoxyalkyl) -2-chloroacetamide.

Example 2

Field Efficiency Studies

On 250 m ² plots, 2.44% organic matter was tested in four replicates. At the beginning of May, Pioneer 3978 maize was sown in well-prepared soil at a depth of 800,000 pieces / ha to a depth of 5-6 cm. On the day following sowing, the plots are shown separately in Table 7 7.

aqueous suspension slurry of 84% by weight sprayable powder (WP) and treated with 4% by weight granulate (G). Haflinger per ^{45 was} used for spraying and Fontane granulate spraying equipment for granule spraying. untreated controls were also set up for comparison. The experiment was evaluated at the beginning of October by counting the Panicum miliaceum bugs in 4x1 rr ² plots and visualizing the corn.

For two consecutive years, we conducted a series of 55 experiments. The results of the first test are shown in Table 8 and the second in Table 9.

spreadsheet

Name of the component

Composition t 7 ° tZ WP 4 tZ G

3 12 3

N- (Dialyl-phenyl) -N- (alkoxyalkyl) -2-chloroacetamide (100% pure) 84 - 36 4 - 1.7

Continuation of Table 7

Name of the component 84 1 Share t% W? 2 e t e t e 1 tZ 4 t 3 G 2 3 3 1 Fluorodifen (100 µL •> f cisztasagu » 84 48 4 2.3 HOE S 1494 (cresol-form dehyde cond. salt) Third 5 3.5 3.5 Cab-O-Sil M5 add. (synthetic silica) 100 100 100 Solvesso 200 (min 97 £ dimethylnaphthalene-containing aromatic solvent) 2 2 2 N- (dichloroacetyl) -1-oxo-4-azaspiro-4,5-decane-bicyclo) 10th 5 - 4.5 0.5 0.2 Stone Country add. (Diaper Ski) - - - 100 100 100

Table 8

preparation name Application rate kg / ha 1 Panicum miliaceum whooping? db / m5 block number in control Z Degree of damage to maize 2 3 4 average Acetochlor 84WP 1.8 42.0 48.2 41.2 53.4 46.2 19.5 no 3.6 18.3 26.3 ' 28.7 32.3 26.4 11.1 permanent distortion, approx. 25Z growth depression Fluoridifen 84 WP 2.4 33.3 72.4 67.5 44.6 55.7 23.5 no acetochlor * 4.8 1.8+ 29.6 34.8 36.3 41.7 35.6 15.4 slight leaf fading + Fluorodifen 84WP Acetochlor * + 2.4 1.8+ 0 0 0.5 3.5 1.0 0.4 no + F1uorodifen 4G + 2.4 0.5 0.5 1 .5 1.5 i .0 0.4 no Kontrol 196.5 205.3 248.2 296.4 236.6 100 a herb that is completely left behind in its development, suppressed by weeds

Table 9

preparation name Application rate kg / ha 1 Panicum miliaceum bug db / m ' 4 average Bug number in control Z Degree of damage to maize 2 3 Acetochlor 84WP 1.8 39.7 42.7 40.8 47.2 42.5 16.6 no Alachlor 84WP 1.8 49.5 40.8 45.3 41.0 44.2 17.2 no D Metachlor 84WP 1.8 53.4 47.3 52.6 45.2 49.6 19.3 no Metolachlor 4G 1.8 43.7 49.8 45.9 50.2 47.4 18.5 no Fluoridifen 84WP Acetochlor * 2.4 1.8+ 58.5 42.7 69.3 37.5 52.0 20.2 no + Fkurodifene 84WP Alachlor + 2.4 1.8+ 0 1.5 0 2.5 1 .0 0.4 no + Fluoridifen 84WP Dimetachlor + + 2.4 1.8+ 0 3.5 2.0 0.5 1.5 0.5 no + Flurorodifen 84WP Metolachlor * + 2.4 1.8+ 0.5 1.5 5.5 2.5 2.5 0.9 no ♦ Flurodifen ^ 6 +2.4 0 1.5 4.5 0 1.5 0.5 no Kontrol 254.7 213.8 273.4 285.4 256.9 00 a herbivore-suppressed herd

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The data in Tables 8 and 9 illustrate that, in areas treated with a dose of 4.2 kg active ingredient / ha, optimal synergistic formulations were able to assure an weed-free state by the end of the growing season, i.e., Panicum miliaceum was virtually absent. preparations proved to be ineffective. Double doses of the individual active ingredients did not effectively control Panicum miliaceum, but did cause some damage to the corn. Formulations of various concentrations and shapes / WP and G / were shown to be equivalent in biological efficacy.

Example 3

Preparation of a synergistic composition in the form of an emulsifiable concentrate.

A 200 L propellant-agitated autoclave with propeller stirrer is charged with 30 kg of cyclohexanone and 14 kg of xylene. Under stirring, 21 kg of 96% technical grade Fluorodifen, 2 kg of N- (dichloroacetyl) -1-oxo-4-azaspirobicyclo-4,5-decane selectivity enhancer are added, followed by 23 kg of % of Acetochlor of technical purity. Mixing at 75 ° C / 75 ° C to 40 ° C gives a clear clear solution to which are added 8 kg of Atlox 4853 and 2 kg of Atlox 4851 homogenised surfactants. Stirring is continued for a further 30 minutes while the product temperature is adjusted to 20 - 10 ^° C. The composition was passed through a 2 micrometer filter.

Example 4

Preparation of a sprayable powder synergistic composition.

In a Lödige M20 vortex mixer, 0.17 kg of Cab-0-Sil M5 carrier was weighed and sprayed with 1.10 kg of 98% pure Alachlor at 60 ± 5 ° C with constant stirring. In a hammer mill, 1.50 kg of the active ingredient Fluordifen, up to 2 mm in diameter and 96% pure, are added to the material in the Lödige M20 mixer and then 0.10 kg of N-dichloroacetyl-l-oxo-4, which increases the selectivity, is added. azaspiro O-bicyclo-4,5-decane; and 0.13 kg HOE S 1494 surfactant.

The formulation homogenized in the Lödige M20 mixer is JMRS-80 tip. swirl jet mill is ground to a portion of the product up to ⁵ to 30 micrometer particle diameter does not exceed 5 weight percent.

Example 5

Preparation of a synergistic composition in the form of sorption granules.

150 g Solvesso 200 Liquid Carrier ¹⁰ dissolved in ¹⁰ g with stirring 59 g 87%

aqueous acetochlor technical grade, 72 g of 96% strength technical-grade fluorodifen enhancing agent and 6 g of N- (dichloroacetyl) -1-οχο-4-azaspiro-4,5-decane-bicyclo selectivity ^{of 15} excipient. A drum mixer was charged with 30 liters Telscig type marked 51 gyöngykovaföldet 2700 g Diaper having a surface sprayed with the previously produced to _20, cooled to 50 ± 5 ° C was heated with stirring.

Claims (2)

CLAIMS 1. A herbicidal composition, wherein the carrier, preferably a polar or apolar organic solvent ^J and / or a mineral or synthetic solid carrier and 0.2-15% by weight of auxiliary agent, is preferably nonionic and / or is present in an amount of 1-95% by weight. y ionic surfactant and / or selectivity enhancer - characterized in that: 30 to 90% by weight of the active ingredient in the total amount of N- (diacid-1-phenyl) -N- (alkoxy-alkyl) -2-chloro-acetamide of the general formula (I) - which in the formula (I) an alkoxyalkyl group in which the alkoxy and alkyl groups ^{35 can be} C 1 -C 4, R ₂ and R ₃ are the same or different C 1 -C 4 alkyl groups, and 2-nitro-1- (4-nitrophenoxy) - Containing 4-trifluoromethylbenzene in a ratio by weight of ⁰ (1: 4) to (2.3:: 1) relative to each other (priority: 25 February 1986) 2. Fibricidal compositions, wherein the carrier comprises from 1 to 95% by weight of a carrier, preferably a polar or apolar organic solvent and / or a mineral or synthetic solid carrier and 0.2-15% by weight of auxiliary agent, preferably a nonionic and / or ionic surfactant; / or selectivity-increasing agent - characterized in that ^50- N- (2'-ether 1-6'-methylphenyl) -N- (ethoxymethyl) -2-chloro is present in an amount of 1-90% by weight as an active ingredient. acetamide and 2-nitro-1- (4-nitrophenoxy) -4- (trifluoromethyl) benzene in a weight ratio of 1: 4 to 2.3: 1.