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GB2163349A - Synergistic herbicidal composition - Google Patents

Synergistic herbicidal composition Download PDF

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Publication number
GB2163349A
GB2163349A GB08516880A GB8516880A GB2163349A GB 2163349 A GB2163349 A GB 2163349A GB 08516880 A GB08516880 A GB 08516880A GB 8516880 A GB8516880 A GB 8516880A GB 2163349 A GB2163349 A GB 2163349A
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GB
United Kingdom
Prior art keywords
nitro
weight
herbicidal composition
ethyl
ethoxymethyl
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Granted
Application number
GB08516880A
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GB2163349B (en
GB8516880D0 (en
Inventor
Dr Ferenc Bihari
Dr Peter Bohus
Gyula Eifert
Edit Halasz
Andras Horvath
Dr Peter Inczedy
Tibor Kovacs
Mihaly Pletyak
Janos Lestyan
Dr Istvan Magyari
Mihaly Nagy
Sandor Szalai
Elemer Tomordi
Laszlo Wohl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Budapesti Vegyimuevek Rt
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Budapesti Vegyimuevek Rt
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Publication of GB8516880D0 publication Critical patent/GB8516880D0/en
Publication of GB2163349A publication Critical patent/GB2163349A/en
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Publication of GB2163349B publication Critical patent/GB2163349B/en
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/26Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A synergistic herbicidal composition which comprises as active ingredient in a total amount of 1-90 % by weight a 1:4-2.3:1 mixture of N-(2'-ethyl-6'-methyl-phenyl)-N-ethoxymethyl-2-chloro-acetamide and 2-nitro-1-(4- nitro-phenoxy)-4-trifluoromethyl benzene, in admixture with usual inert solid or liquid carriers and auxiliary agents, is particularly useful for selectively combating Panicum miliaceum in maize cultures.

Description

SPECIFICATION Synergistic herbicidal composition This invention relates to a synergistic herbicidal composition, a processforthe preparation thereof and the use ofthe said composition in agriculture for combating weeds.
The present invention is based on the recognition that N - (2' - ethyl ethyl - 6'- methyl - phenyl) - N - ethoxymethyl - 2 - chloro - acetamide (ACETOCHLOR) and 2 - nitro -1 -(4- nitro -phenoxy)-4- trifluoromethyl - benzene (FLUORODIPHEN) exhibit synergistic effect.
The active ingredient components ofthesynergis- tic herbicidal composition ofthe present invention are known per se. Thus the preparation of ACETOCH LOR is described in US patent No. 3,442,945 and that of FLUORODIPHEN is disclosed in British patent No.
1,033,163.
Hitherto herbicidal compositions comprising chloro amino triazine derivatives were most widespreadly used for combating weeds occurring in maize cultures. The disadvantage ofthe said herbicidal compositions is that they are inactive against certain monocotyledonous weeds, since the said weeds, similarly to maize, are capable of detoxicating the herbicidal active ingredients/See K.I.N. Jensen; G.R. Stephensen and L.A. Hunt: "Detoxification of atrazin in three Gramineae subfamilies" (Weed Sci.) Champaign, III., 1977., Vol. 25, pages 212-220.1.
It is known that second to maize it is Panicum miliaceum which is most capable of detoxicating the herbicide atrazin and this is the reason why the said weed strain is so widespread. Other herbicides generally used in maize cultures (thiourea and urea derivatives, acetanilides, etc.) are not sufficiently effective against Panicum iliaceum either.
Several effortswere madeto combate the above dangerous weed species and various compositions and biological procedures were elaborated. Encouraging results were however obtained only by post-emergent treatment.
It is the object of the present invention to provide a herbicidal composition and method suitable for effectively combating Panicum miliaceum weed species.
It has been found in a surprising mannerthat combinations comprising Acetochlor and Fluorodiphen in certain ratios exhibit a herbicidal effect which is superiorto the sum of the effect ofthe components used per se i.e. the compositions of the present invention possess synergistic properties.
According to the present invention there are provided herbicidal composition comprising as active ingredient in a total amount of 1-90 % by weight a 1:4-2.3:1 mixture of N - (2' - ethyl -6' - methyl - phenyi) - N - ethoxymethyl - 2 - chloro - acetamide and 2 - nitro -1 -(4- nitro- phenoxy} - 4 - trifl uoro - methyl benzene in admixture with usual inert solid or liquid carriers and auxiliary agents.
The liquid carrier may be an aliphatic and/or aromatic hydrocarbon, alcohol, ketone, ester, prefer ablyxylene orcyclohexanone. The solid carrier may be any suitable natural mineral, preferably silicic acid, China-clay, caolin, ground limestone and/or a synthetic silicate.
The compositions of the present invention may comprise suitable wetting and/or dispersing agents, non-ionic and/or anionic surfactants, lignine sulfonic acid derivatives, adhesives or the selectivity improving agents, etc.
The compositions ofthe present invention may be finished in any suitable form applicable in agriculture or horticulture e.g. in the form of in water emulsifiable concentrate, wettable powder, dusting powder, granule, etc.
The emulsifiable concentrate and wettable powder may be diluted with water to provide a ready-use spray, while the granules may be directly applied onto the soil and used in a pre-emergent manner. The optimal dose amounts to about 1 kg of total active ingredient/ha under culturing vessel conditions.
The compositions according to the present invention can be preferably used for combating monocotyledonous weeds without damaging the cultivated plants. The compositions are particularly useful due to their selective activity in maize cultures against panicum miliaceum.
The activity tests are carried out by usual and well-known methods/L. Bånki: "Bioassay of pesticides in the laboratory", Akadbmiai Kid6, Budapest, 1978, pages 292-302; J.G. Horsfall (1945), "Fungicides and their action", Walthem, Mass USA Chronica Botanica; Scandari (1962): "Sinergismo di efficacia anticritlogamica tra Maneb e zolfo o polisolfuro di bario o Thiram", Notiz Malatt, Plante 61,3-35,37-48, 53-69/. These methods are particularly suitable for the determinations of the simultaneous-- i.e. synergistic, additive or antagonistic -- effect of two bioactive compounds.
In Figure 1 the following activity data of ACETOCH LOR (A) and FLUORODIPHEN (F) against Panicum miliaceum are shown: measured activity of the components when used perse; - expected effect (on the basis ofthe per se measured data); - measured activity of the combination of the two compo ents.
It appears from Figure 1 that at the preferable active ingredient ratio the measured activity of the combination is by more than 30 % higher than the expected value and this clearly proves the synergistic surpluseffect.
The unforeseen and surprising advantage ofthe synergistic composition of the present invention resides in the factthat it enables a highly efficient and safe pre-emergent protection against Panicum miliaceum in maize culture by using a relatively small pesticidal dose whereby the cultivated plant is nor damaged even to the slightest extent.
Further details ofthe composition ofthe present invention and the biological activity thereof are shown in the following non-limiting Examples with out limiting the scope of protection to the said Examples.
Example 1 Glasshousetests in a cultivating pot 9 kg of a 1:1 mixture of field soil and sand soil are placed in cultivating pots (30 x 30 x 30 cm), whereupon 100 MVSC 1295 (FAO 200) maize hybrides and 100 Panicum miliaceum weed-seeds a re sown into each pot in a depth of 4 cm and 2 cm, respectively. The surface of the soil is treated with an emulsion spray prepared by dilating with water an emulsifiable concentrate (EC) having the composition disclosed in Table 1 and containing 50 % by weight of the active ingredient. The doses and results of the activity test are summarized in Tables 2-4.
Plants nottreated with thetestcompositions serve as control. During the test the temperature of the glass house is maintained at 15-25 C, the strength of illumination amounts to 24 klux, the intensity is 70 W.m-2 and the relative humidity content amounts to 80%.
The results are evaluated 15 days after shooting.
The state and condition of the plants is expressed with the aid ofthefollowing bonityscale: 0 = no damages; 1 = not more than 25 % of the leaves are damaged; 2 = the distortion (deformation) ofthe leaves and the growth inhibition is not largerthan 50 %; 3 = the distortion (deformation) of the leaves and the growth inhibition is not higherthan 75 %; 4 = complete, 100 % death of the leaves.
Table 1 Composition, % by weight Component 1 2 3 4 5 6 7 8 9 10 11 ACETOCHLOR Cico %) 40 - 4 8 12 16 20 24 28 32 36 PLUORDIZEN Cioo f) - 40 36 32 28 24 20 16 12 8 4 Surfactant (ATLOX 4853) 8 8 8 8 8 8 8 8 8 8 8 Surfactant (ATLOX 4851) 2 2 2 2 2 2 2 2 2 2 2 Additive for increas ing selectivity;; N- -(dichloro-acetyl)-l -oxo-4-azaspiro-bicye- 4 - 0,4 0,8 1,2 1,6 2,0 2,4 2,8 3,2 3,6 10-4 ,5-decane Cyelohexanone, solvent 30 30 30 30 30 30 30 30 30 30 30 Xylene solvent, add. 100 100 100 100 100 100 100 100 100 100 100 Table 2 Activity of ACETOCHLOR (Composition 1) against Panicum miliaceum in cultivating pots ACL0CIfL0R Rate of damages of Pani- Damages Maize, rate of damages Damages dose con miliaceun (100 plants) total (from 100 plants) total ChL'/bn) O 1 2 3 4 (%) 0 1 2 0,2 35 20 18 12 15 38,0 100 0 0 0 0,4 27 24 20 14 15 41,5 95 5 0 1,25 o,6 21 28 18 16 17 45,0 92 8 0 2,0 0,8 2 28 22 24 24 62,5 90 10 2,5 1,0 0 10 24 34 32 72,0 82 12 4 5,0 1,2 0 0 24 36 40 79,0 80 12 6 6,0 1,4 0 0 8 32 60 88,0 70 24 6 9,0 1,6 0 0 0 8 92 98,0 56 28 1G 15,0 Control 100 0 0 0 0 0 100 0 0 0 Table 3 Activity of FLUORODIPHEN (Composition 2) against Panicum miliaceum in cultivating plants FLUORODIPHEN Rate of damages cf Panicum Damages Maize, rete of damages Damages dose miliaceum (from 100 plants) total (from 100 plants) total (kg/la) 0 1 2 3 (%) 0 1 2 (%) 0,2. 16 60 24 0 . 0 27,0 100 0 0 0 0,4 2 64 34 0 0 33,0 100 0 0 0 0,6 0 32 52 lo 0 46,0 100 0 0 0 0,8 0 16 60 28 0 55,0 100 0 0 0 1,0 0 0 48 52 0 63,0 100 0 0 0 1,2 0 0 22 68 10 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 40 85,0 90 10 0 2,5 Control 100 0 0 0 0 0 100 0 0 0 Table 4 Activity of a combination ACETOCHLOR+FLUORODIPHEN against Panicum miliaceum in cultivating pots Com- AOETOCHLOR+ Rate of damages of Panicum Maize, rate of Damages po- + FLUORODIPHEN miliaceum (from 100 plants) Damages damages (from total Si- dose tion (g/ha) 0 1 2 3 4 total 100 plants) 0 1 2 3 4 (%) 0 1 2 3. 0,1+0,9 0 0 20 68 12 73,0 100 0 0 0 4. 0,2+0,8 0 0 0 68 32 83,0 100 0 0 0 5. 0,3+0,7 0 0 0 12 88 97,0 100 0 0 0 6. 0,4+0,6 0 0 0 0 100 100,0 95 5 0 1,25 7. 0,5+0,5 0 0 0 0 100 100,0 95 5 0 1,25 8. 0,6+0,4 0 0 0 24 76 94,0 92 8 0 2,0 9. 0,7+0,3 0 0 24 36 40 79,0 92 8 0 2,0 10. 0,8+0,2 0 0 30 40 30 75,0 90 10 0 2,5 11. 0,9+0,1 0 25 46 29 68,5 88 12 0 3,0 Control 100 0 0 0 0 0 100 0 0 0 The data of Tables 2-4 show unambiguously that combinations of Acetochlorand and Fluorodiphen exhibit synergistic effect in the complete dose range offrom 0.2 + 0.8 kg/ha to 0.7 + 0.3 kg/ha i.e. between the active ingredient ratio limits of from 1 :4to 2.3:1.Best results are obtained atan active ingredient ratio of 1:2 -1:1.
Example 2 Field tests Thetests are carried out on plots having a plot-size of 250 m2, in soil having an organic substance content of 2.44 % and in four replicates. Inthethoroughly homogenized soil at the beginning of May 800,000 seeds/h a of maize/Pioneer 3978/are shown at a depth of 5-6 cm.The day following the sowing the plots are treated separately with an aqueous suspension spray prepared from the 80 % by weight wettable powder (WP) having the composition according to Table 5 and with 4 % by weight granule(G).Sprayingis carried out by using a Haflinger spraying machine and the granules are spread with the aid of a Fontane granule spreading apparatus. Untreated plants serve as control.The test is evaluated at the beginning of October by counting the panicum miliaceum panicles on an area of 4 x 1 m2 on each parcel and visually evaluating the symptoms of damages on maize.
The results are summarized in Table 6.
Table 5 Composition, % by weight 84 "6,wP 4 % C Component 12 13 14 15 16 17 Acetochior (pure) 84 - 36 4 4 1,7 Pluorodiphen (pure) - 84 48 - 4 2,3 Hoe S 1494 (eresol and formaldehyde condensate, salt) 3,5 3,5 3,5 - - - Cab-O-Sil M5 Add.
(synthetic silicic acid) 100 100 100 - - Solves30 200 - - - 2 2 2 N-(dichloroacetyl)-l- -oso-4-azaspiro-bicyc- 10-4,5-dekane 10,5 - 4,5 0,5 - 0,2 Silicic acid add, - - - 100 100 100 (Diaperl 51) Table 6 Active in- Panicum miliac m No. ol panic- Rate of damages Composition gredient panicles,NoI lea control as omposiion gredient panicles, 2 3 4 Average % of control on maize Acetochior 1,8 42,0 48,2 41,2 53,4 46,2 19,5 no 84WP(comp.l2) 3,6 18,3 26,3 28,7 32,3 26,4 11,1 final deformation growth depression Pluorodiphen 2,4 33,3 72,4 67,5 44,6 55,7 23,5 no about 25 % 84WP (comp.l3) 29,6 34,8 36,3 41,7 35,6 15,4 alight discolora- tion of leaves Acetochlor+ 1,8 + Pluorodiphen 84wP (eomp.1+2,4 0 0 0,5 3,5 1,0 0,004 no Aeetoehlor+ 1,8 ± + Fluorodiphen +2,4 0,5 0,5 1,5 1,5 1,0 0,004 no completely underde Control - 196,5 205,3 248,2 296,4 236,6 100 velopped stock, supp ressed by the weeds The data of Table 6 show that plots treated with a dose of 4.2 kg of active ingredient/ha of the synergistic combination were substantially free of Panicum miliaceum during the complete cultivating period i.e. the dangerous weed was practically completely eliminated. On the other hand treatment carried out by using the said active ingredients separately was completely ineffective. Ifthe components are applied verse in double doses (i.e 100 % excess) the Panicum miliaceum is not effectively combated moreover certain damages of maize are observed.
Differentformulations ofvarying concentrations (WP and G) proved to be equivalentfrom the pointofview of biological activity.

Claims (4)

1. Herbicidal composition comprising as active ingredient in a total amount of 1 -90 % by weight a 1:4 -2.3:1 mixture of N - (2' - ethyl - 6' - methyl - phenyl) - N - ethoxymethyl - 2 - chloro - acetamide and 2 - nitro - 1 -(4- nitrophenoxy) -4-tri -fluoromethyl - benzene in admixture with usual inert solid or liquid carriers and auxiliary agents.
2. Herbicidal composition according to Claim 1 comprising a liquid carrier in atotal amountof40-90 % % by weight one or more aliphatic and/or aromatic hydrocarbon(s), alcohol(s), ketone(s) and/or ester(s), preferably xylene or cyclohexanone, and/or as solid carrierin a total amountof40-90 % by weight one or more natural mineral(s), preferablysilicic acid Chineclay, Kaolin, ground limestone and/or artificial synth eticsilicate(s).
3. Herbicidal composition according to Claim 1 comprising as auxiliary agent in a total amount of 0.5-15 by weight of one or more wetting and/or dispersing agent(s) and/or non-ionic and/or anionic surfactant(s) oradhesive(s) and/or selectively improving agent(s).
4. Method for combating weeds which comprises applying onto the plants or environment thereof an effective amount of a combination of N - (2' - ethyl -6' - methyl - phenyl) - N -ethoxymethyl - 2 - chloro acetamide and 2 - nitro - 1 - (4 - nitro - phenoxy) - 4 -trifluoromethyl - benzene.
5 Use of a combination of N - (2' - ethyl - 6' methyl - phenyl) - N -ethoxymethyl -2 -chloro acetamide and 2 - nitro - 1 - (4- nitro - phenoxy) -4 trifluoromethyl - benzene for combating weeds.
GB08516880A 1984-07-17 1985-07-03 Synergistic herbicidal composition Expired GB2163349B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU842773A HU193214B (en) 1984-07-17 1984-07-17 Synergic herbicide compositions for extirpating panicum miliaceum containing chloro-acetamide derivatives and substituted benzene derivatives as active agents

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GB8516880D0 GB8516880D0 (en) 1985-08-07
GB2163349A true GB2163349A (en) 1986-02-26
GB2163349B GB2163349B (en) 1988-05-05

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BR (1) BR8503390A (en)
CH (1) CH664258A5 (en)
CS (1) CS261226B2 (en)
DD (1) DD235553A5 (en)
DE (1) DE3525371A1 (en)
ES (1) ES8608282A1 (en)
FR (1) FR2567718B1 (en)
GB (1) GB2163349B (en)
HU (1) HU193214B (en)
IT (1) IT1207061B (en)
PL (1) PL143071B1 (en)
RO (1) RO93277A (en)

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RU2147802C1 (en) * 1998-11-16 2000-04-27 Всероссийский научно-исследовательский институт люпина Herbicide composition
DE19958381A1 (en) 1999-12-03 2001-06-07 Bayer Ag Herbicides based on N-aryl-uracils

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* Cited by examiner, † Cited by third party
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BE628133A (en) * 1962-02-08
GB1407205A (en) * 1971-09-17 1975-09-24 Girling Ltd Vehicle braking systems
JPS5350328A (en) * 1976-10-16 1978-05-08 Kumiai Chem Ind Co Ltd Composition for herbicides
JPS5555107A (en) * 1978-10-19 1980-04-22 Nissan Chem Ind Ltd Herbicidal composition
TW286443B (en) * 1994-10-25 1996-09-21 Fridolin Alois Frech

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PL254561A1 (en) 1986-06-17
FR2567718B1 (en) 1988-10-14
DD235553A5 (en) 1986-05-14
CS261226B2 (en) 1989-01-12
FR2567718A1 (en) 1986-01-24
RO93277B (en) 1987-12-31
CH664258A5 (en) 1988-02-29
PL143071B1 (en) 1988-01-30
HU193214B (en) 1987-08-28
HUT39565A (en) 1986-10-29
ES8608282A1 (en) 1986-07-16
GB2163349B (en) 1988-05-05
CS530685A2 (en) 1988-05-16
RO93277A (en) 1988-03-30
GB8516880D0 (en) 1985-08-07
BR8503390A (en) 1986-04-08
ES545327A0 (en) 1986-07-16
JPS6193103A (en) 1986-05-12
IT8521575A0 (en) 1985-07-16
DE3525371A1 (en) 1986-07-10
IT1207061B (en) 1989-05-17

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