WO1994018837A1 - Herbicidal compositions - Google Patents

Herbicidal compositions Download PDF

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Publication number
WO1994018837A1
WO1994018837A1 PCT/EP1994/000571 EP9400571W WO9418837A1 WO 1994018837 A1 WO1994018837 A1 WO 1994018837A1 EP 9400571 W EP9400571 W EP 9400571W WO 9418837 A1 WO9418837 A1 WO 9418837A1
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WO
WIPO (PCT)
Prior art keywords
galap
viola
ethylhexyl
phosph
onate
Prior art date
Application number
PCT/EP1994/000571
Other languages
French (fr)
Inventor
Martin Mach
Bernd Fischer
Jürgen Bohner
Richard Rees
Original Assignee
Schering Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Priority to EP94909081A priority Critical patent/EP0684766B1/en
Priority to DE69402691T priority patent/DE69402691D1/en
Publication of WO1994018837A1 publication Critical patent/WO1994018837A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • This invention relates to new herbicidal compositions and methods of combating weeds.
  • Prior Art US Patent No 2927014 discloses phosphonates and phosphinates having herbicidal activity. We have now found that combinations of one specific compound according to the US Patent with certain known herbicides are surprisingly beneficial and synergistic.
  • the invention provides new herbicidal compositions with synergistic activity that comprise as active materials a mixture of (a) 0,0-bis(2-ethylhexyl) (2-ethylhexyl)phosphonate, and (b) a herbicide selected from the group of thidiazimin (b ⁇ ,
  • N-(4-chloro-2-ethyl-6-fluorobenzothiazol-7-yl)- l-cyclohexene-l,2-dicarboximide (b 3 ) , amidosulfuron (b 4 ) , mecoprop-P (b 5 ) , isoproturon (b 6 ) , chlorotoluron (b 7 ) , benazolin-ethyl (b 8 ) , glyphosate (b 9 ) , metsulfuron (b 10 ) , tribenuron (b n ) , thifensulfuron (b 12 ) , and bifenox (b 13 ) .
  • Mecoprop-P is usually present as a salt, especially the potassium salt.
  • Glyphosate is usually present as the isopropylammonium salt but can also be present for example as the trimesium (trimethylsulfonium) salt.
  • Metsulfuron, tribenuron and thifensulfuron are usually present as the methyl esters.
  • the combinations are applied post-emergently.
  • the total amount of active ingredients used in the mixture lies between 10 and 1000 g/ha.
  • the weight ratio of component a) to b) is generally between 20:1 and 1:20, preferably between 10:1 and 1:1.
  • An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents and oils.
  • suitable adjuvants such as organic solvents, wetting agents and oils.
  • Such additives may allow a decrease in the dose.
  • active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants.
  • Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and other mineral-oil fractions and plant oils.
  • Suitable solid carriers include mineral earths, e.g. bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
  • mineral earths e.g. bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
  • surface-active agents there can be used for example calcium lignosulfonate, polyoxyethylenealkylphenyl ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, as well as substituted benzenesulfonic acids and their salts.
  • compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
  • the agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1,000 1/ha.
  • the agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
  • formulations can be carried out in known manner, for example by milling or mixing processes.
  • individual components can be mixed just before use for example by the so-called commonly used tan -mixing method.
  • BRSNW Brassica napus
  • Example 1 The Examples are field tests carried out post-emergently in the Autumn on winter cereals. The compositions are evenly applied to the plants as suspensions using a water amount of 500 litres per hectare. For Examples 1-3 and 13 evaluation was carried out 15 days after application and for Examples 4-12, evaluation was carried out 30 days after application. The evaluation of the individual components (a) and (b) as well as their mixtures was carried out on a scale where 0 is no damage and 100 is complete destruction of the plants.

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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

The invention relates to a new herbicidal composition with synergistic activity which comprises, as active components, a mixture of O,O-bis(2-ethylhexyl)-(2-ethylhexyl)phosphonate, and specified herbicides.

Description

Title: Herbicidal compositions
Field of the invention
This invention relates to new herbicidal compositions and methods of combating weeds.
Prior Art US Patent No 2927014 discloses phosphonates and phosphinates having herbicidal activity. We have now found that combinations of one specific compound according to the US Patent with certain known herbicides are surprisingly beneficial and synergistic.
Description
The invention provides new herbicidal compositions with synergistic activity that comprise as active materials a mixture of (a) 0,0-bis(2-ethylhexyl) (2-ethylhexyl)phosphonate, and (b) a herbicide selected from the group of thidiazimin (b^ ,
2-[7-fluoro-3-oxo-4-(2-propynyl)-3 ,4-dihydro-2H-
1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridine- 1,3-dione (b2) ,
N-(4-chloro-2-ethyl-6-fluorobenzothiazol-7-yl)- l-cyclohexene-l,2-dicarboximide (b3) , amidosulfuron (b4) , mecoprop-P (b5) , isoproturon (b6) , chlorotoluron (b7) , benazolin-ethyl (b8) , glyphosate (b9) , metsulfuron (b10) , tribenuron (bn) , thifensulfuron (b12) , and bifenox (b13) .
The short names quoted for these compounds are the non- proprietary common names and the chemical structure can be found for example by reference to the "Pesticide Manual", ninth edition, 1991, published by the British Crop Protection Council. Of those not mentioned in the Pesticide Manual the full chemical names are as follows: thidiazimin - 6-(6,7-dihydro-6,6-dimethyl-3H,5H- pyrrolo[2,1-c] [1,2,4]thiadiazol- 3-ylidenimino)-7-fluoro- 4-(2-propyny1)-2H-1,4-benzoxazin- 3(4H)-one. amidosulfuron - 3-[4,6-dimethoxypyrimidin-2-yl)-
1-(N-methyl-N-methylsulfonyl- aminosulfonyl)urea, (disclosed in EP 131 258) . Compounds b: and b2 are disclosed in EP 311 135 and compound b3 is disclosed in PCT WO 9220675.
Mecoprop-P is usually present as a salt, especially the potassium salt. Glyphosate is usually present as the isopropylammonium salt but can also be present for example as the trimesium (trimethylsulfonium) salt. Metsulfuron, tribenuron and thifensulfuron are usually present as the methyl esters.
The combination of (a) and (b) can be used for example against the following plant species:
Dicotyledonous weeds of the species Sinapiε, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopod±um, Braεsica, Urtica, Senec±o, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduuε, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopεiε, Papaver, Centaurea and Chrysanthemum and also monocotyledonous weeds of the species Avena, Alopecuruε, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleuεine, Brachiaria, Lolium, Bromus, Cyperuε, Agropyron, Sagittaria, Monocharia, Fimbriεtyliε, Eleocharis, Jsci.ae-7.u-7. and Apera .
The combinations are applied post-emergently. The total amount of active ingredients used in the mixture lies between 10 and 1000 g/ha.
The weight ratio of component a) to b) is generally between 20:1 and 1:20, preferably between 10:1 and 1:1.
An improvement in the intensity and speed of action can be obtained, for example, by addition of suitable adjuvants, such as organic solvents, wetting agents and oils. Such additives may allow a decrease in the dose.
The designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers and/or diluents and, optionally, binding, wetting, emulsifying and/or dispersing adjuvants.
Suitable liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide and other mineral-oil fractions and plant oils.
Suitable solid carriers include mineral earths, e.g. bentonite, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and plant products, e.g. flours.
As surface-active agents there can be used for example calcium lignosulfonate, polyoxyethylenealkylphenyl ethers, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, as well as substituted benzenesulfonic acids and their salts.
The percentage of the active ingredient(s) in the various preparations can vary within wide limits. For example, the compositions can contain about 10 to 90 percent by weight active ingredients, and about 90 to 10 percent by weight liquid or solid carriers, as well as, optionally up to 20 percent by weight of surfactant.
The agents can be applied in customary fashion, for example with water as the carrier in spray mixture volumes of approximately 100 to 1,000 1/ha. The agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
The preparation of these formulations can be carried out in known manner, for example by milling or mixing processes. Optionally, individual components can be mixed just before use for example by the so-called commonly used tan -mixing method.
The following Examples illustrate the use of compositions of the invention. Since the phosphonate (a) when applied on its own shows no herbicidal activity, the expected value for an additive effect according to Colby (S R Colby "Calculating Synergistic and.Antagonistic Response to Herbicide Combinations", Weeds, 15/1, 1967 pages 20 to 22) corresponds to the activity level of the herbicides b1 - b13 without addition of the phosphonate (a) . In the Examples GALAP = Galium aparine VIOAR = Viola arvensis
MATCH = Matricaria chamomilla STEME = Stellaria media BRSNW = Brassica napus
Compounds b10, bn and b1 are used as the methyl ester, compound b9 as the isopropylammonium salt and compound b5 as the potassium salt.
The Examples are field tests carried out post-emergently in the Autumn on winter cereals. The compositions are evenly applied to the plants as suspensions using a water amount of 500 litres per hectare. For Examples 1-3 and 13 evaluation was carried out 15 days after application and for Examples 4-12, evaluation was carried out 30 days after application. The evaluation of the individual components (a) and (b) as well as their mixtures was carried out on a scale where 0 is no damage and 100 is complete destruction of the plants. Example 1
% Control
Herbicide Phosph- g ai/ha GALAP MATCH STEME onate
(b,) 10 47 50 70
(a) 24 0 0 0
(a) 48 0 0 0
(b,) + (a) 10 + 24 84 68 87
(b,) + (a) 10 + 48 95 77 90
Example 2
% Control
Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b2) 15 35 37 27 90
(a) 48 0 0 0 0
(a) 95 0 0 0 0
(b2) + (a) 15 + 48 72 94 30 100
(b2) + (a) 15 + 95 77 95 35 99
Example 3
% Control
Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b3) 15 33 83 20 99
(a) 48 0 0 0 0
(a) 95 0 0 0 0
(b3) + (a) 15 + 48 67 92 23 100 (b3) + (a) 15 + 95 73 90 35 100
Example 4
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b4) 12 42 20 40 55
(a) 48
(b4) + (a) 12 + 48 60 48 63 70
Example 5
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b5) 600 53 18 60 63
(a) 48 0
(b5) + (a) 600 + 48 70 25 73 87 Example 6
% Control
Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b6) 750 13 30 55 83
(a) 48 0
(b6) + (a) 750 + 48 20 37 63 90
Example 7
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b7) 750 15 23 85 88
(a) 48 0
(b7) + (a) 750 + 48 23 37 93 95
Example 8
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME onate
(b8) 200 18 22 88
(a) 48 0
(bo) + (a) 200 + 48 33 30 95 Example 9
% Control
Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b9) 50 20 10 25 28
(a) 48
(b9) + (a) 50 + 48 33 15 38 40
Example 10
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
Figure imgf000011_0001
(a) 48 0
(b10) + (a) 3 + 48 25 58 100 100
Example 11
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(*>11> 15 47 40 78 88
(a) 48 0
(bn) + (a) 15 + 48 55 52 88 95 Example 12
% Control
Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(b12) 24 58 48 70 88
(a) 48
(b12) + (a) 24 + 48 73 52 75 96
Example 13
% Control Herbicide Phosph- g ai/ha GALAP VIOLA STEME MATCH onate
(*»13> 500 78 95 15 63
(a) 48
(b13) + (a) 500 + 48 88 98 20 78

Claims

1. Herbicidal compositions with synergistic activity that comprise as active materials a mixture of
(a) 0,0-bis(2-ethylhexyl) (2-ethylhexyl)phosphonate, and (b) a herbicide selected from the group of thidiazimin (bj) ,
2-[7-fluoro-3-oxo-4-(2-propynyl) -3,4-dihydro-2H-
1,4-benzoxazin-6-yl]perhydroimidazo[1,5-a]pyridine-
1,3-dione (b2) , N-(4-chloro-2-ethyl-6-fluorobenzothiazol-7-yl)- l-cyclohexene-l,2-dicarboximide (b3) , amidosulfuron (b4) , mecoprop-P (b5) , isoproturon (b6) , chlorotoluron (b7) , benazolin-ethyl (b8) , glyphosate (b9) , metsulfuron (b10) / tribenuron (b ) , thifensulfuron (b12) , and bifenox (b13) .
2. A composition according to claim 1 in which the weight ratio of (a) to (b) is between 20:1 to 1:20.
3. A composition according to claim 2 in which the weight ratio of (a) to (b) is between 10:1 to 1:1.
4. A method of combating weeds which comprises applying to the words and their locus a composition as claimed in any one of the preceding claims.
5. A method according to claim 4 in which there is used a total amount of active ingredients of 10 to 1000 g/ha.
PCT/EP1994/000571 1993-02-20 1994-02-17 Herbicidal compositions WO1994018837A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94909081A EP0684766B1 (en) 1993-02-20 1994-02-17 Herbicidal compositions
DE69402691T DE69402691D1 (en) 1993-02-20 1994-02-17 HERBICIDAL COMPOSITIONS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4305542.7 1993-02-20
DE4305542A DE4305542C1 (en) 1993-02-20 1993-02-20 Herbicidal agents with synergistic effects

Publications (1)

Publication Number Publication Date
WO1994018837A1 true WO1994018837A1 (en) 1994-09-01

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Family Applications (1)

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Country Status (5)

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EP (1) EP0684766B1 (en)
AT (1) ATE151598T1 (en)
CA (1) CA2156494A1 (en)
DE (2) DE4305542C1 (en)
WO (1) WO1994018837A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003099012A1 (en) * 2002-05-23 2003-12-04 Syngenta Limited Phosphonates and derivatives thereof as enhancers of the activity of insecticides
WO2003105589A1 (en) * 2002-06-13 2003-12-24 Syngenta Limited Composition comprising a cyclohexanedione herbicide and an adjuvant
WO2008049618A3 (en) * 2006-10-27 2009-03-26 Syngenta Participations Ag Herbicidal compositions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927014A (en) * 1957-02-14 1960-03-01 Virginia Carolina Chem Corp Method for killing plants
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
EP0311135A2 (en) * 1987-10-09 1989-04-12 Schering Aktiengesellschaft Heterocyclic substituted azoles and azines, process for their preparation and their use as an agent with herbicide activity
WO1992020675A1 (en) * 1991-05-24 1992-11-26 Schering Aktiengesellschaft Substituted benzothiazole derivatives, their preparation and use as herbicides
WO1993004585A1 (en) * 1991-08-30 1993-03-18 Schering Aktiengesellschaft Herbicidal compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1809062A1 (en) * 1968-11-15 1970-06-04 Hoechst Ag Stabilisers for 4,6-dinitro-2-sec butyl phenol esters
DK137879A (en) * 1978-04-12 1979-10-13 Sandoz Ag FLOODING AGENT
IL77817A (en) * 1986-02-06 1995-06-29 Yeda Res & Dev Process for controlling plant growth and herbicidal compositions therefor

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927014A (en) * 1957-02-14 1960-03-01 Virginia Carolina Chem Corp Method for killing plants
US3929450A (en) * 1974-06-28 1975-12-30 Monsanto Co Herbicidal compositions and methods
EP0311135A2 (en) * 1987-10-09 1989-04-12 Schering Aktiengesellschaft Heterocyclic substituted azoles and azines, process for their preparation and their use as an agent with herbicide activity
WO1992020675A1 (en) * 1991-05-24 1992-11-26 Schering Aktiengesellschaft Substituted benzothiazole derivatives, their preparation and use as herbicides
WO1993004585A1 (en) * 1991-08-30 1993-03-18 Schering Aktiengesellschaft Herbicidal compositions

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9138003B2 (en) 2002-05-23 2015-09-22 Syngenta Crop Protection Inc. Phosphonates and derivatives thereof as enhancers of the activity of insecticides
AU2003227965B9 (en) * 2002-05-23 2003-12-12 Syngenta Limited Phosphonates and derivatives thereof as enhancers of the activity of insecticides
JP2005531567A (en) * 2002-05-23 2005-10-20 シンジェンタ リミテッド Phosphonates and their derivatives as activity enhancers of insecticides.
CN100333643C (en) * 2002-05-23 2007-08-29 辛根塔有限公司 Phosphonates and derivatives thereof as enhancers of the activity of insecticides
AU2003227965B2 (en) * 2002-05-23 2007-10-04 Syngenta Limited Phosphonates and derivatives thereof as enhancers of the activity of insecticides
WO2003099012A1 (en) * 2002-05-23 2003-12-04 Syngenta Limited Phosphonates and derivatives thereof as enhancers of the activity of insecticides
WO2003105589A1 (en) * 2002-06-13 2003-12-24 Syngenta Limited Composition comprising a cyclohexanedione herbicide and an adjuvant
WO2008049618A3 (en) * 2006-10-27 2009-03-26 Syngenta Participations Ag Herbicidal compositions
EA016230B1 (en) * 2006-10-27 2012-03-30 Зингента Партисипейшнс Аг Herbicidal compositions
KR101494629B1 (en) 2006-10-27 2015-02-23 신젠타 파티서페이션즈 아게 Herbicidal compositions
JP2010507611A (en) * 2006-10-27 2010-03-11 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Herbicidal composition
AP3424A (en) * 2006-10-27 2015-09-30 Syngenta Ltd Herbicidal compositions
US9414593B2 (en) 2006-10-27 2016-08-16 Syngenta Crop Protection, Llc Herbicidal compositions

Also Published As

Publication number Publication date
EP0684766B1 (en) 1997-04-16
ATE151598T1 (en) 1997-05-15
EP0684766A1 (en) 1995-12-06
DE69402691D1 (en) 1997-05-22
DE4305542C1 (en) 1994-07-21
CA2156494A1 (en) 1994-09-01

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