WO1993005655A1 - Synergistic herbicidal compositions - Google Patents

Synergistic herbicidal compositions Download PDF

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Publication number
WO1993005655A1
WO1993005655A1 PCT/EP1992/002185 EP9202185W WO9305655A1 WO 1993005655 A1 WO1993005655 A1 WO 1993005655A1 EP 9202185 W EP9202185 W EP 9202185W WO 9305655 A1 WO9305655 A1 WO 9305655A1
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Prior art keywords
methyl
common name
dimethyl
mixture
fluoro
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1992/002185
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French (fr)
Inventor
Gerhard Johann
David Gillham
Richard Rees
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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Filing date
Publication date
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Priority to JP5505798A priority Critical patent/JPH06510775A/en
Priority to FI941330A priority patent/FI941330A0/en
Priority to EP92919951A priority patent/EP0605533A1/en
Priority to AU25891/92A priority patent/AU652481B2/en
Priority to BR9206527A priority patent/BR9206527A/en
Priority to SK336-94A priority patent/SK33694A3/en
Publication of WO1993005655A1 publication Critical patent/WO1993005655A1/en
Priority to BG98672A priority patent/BG98672A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • This invention relates to a new herbicidal composition having synergistic activity comprising a mixture of
  • the herbicidal activity of the combination of the active ingredients of the invention is essentially higher than the individual components and also of the sum of the individual components. A synergistic effect is also seen.
  • imazamethabenz triasulfuron, amidosulfuron, ethofumesate, diflufenican, tribenuron-methyl, mecoprop, 2,4-D,
  • Cyanazine is the common name for 2-chloro-4-(1-cyano- 1-methylethylamino)-6-ethylamino-1,3,5-triazine;
  • ioxynil is the common name for 4-hydroxy-3,5-diiodo- benzonitrile
  • isoproturon is the common name for 3-(4-isopropylphenyl)- 1,1-dimethylurea;
  • methabenzthiazuron is the common name for 1-(benzothiazol- 2-yl)-1,3-dimethylurea;
  • bifenox is the common name for methyl 5-(2,4-dichloro- phenoxy)-2-benzoate
  • chlorsulfuron is the common name for 1-(2-chlorophenyl- sulfonyl)-3-(4-methoxy-3-methyl-1,3,5-triazin-2-yl)urea; metsulfuron-methyl is the common name for methyl
  • thifensulfuron-methyl is the common name for methyl
  • isoxaben is the common name for N-[3-(1-ethyl-1-methyl- propyl)isoxazol-5-yl]-2,6-dimethoxybenzamide;
  • imazamethabenz is the common name for 2-[4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)-4 (5) -methylbenzoate; triasulfuron is the common name for 1-(2-chlorethoxy)-
  • amidosulfuron is the common name for 1-(4,6-dimethoxy- pyrimidin-2-yl)-3-(N-methyl-N-methylsulfonylsulfamoyl)- urea;
  • ethofumesate is the common name for 2-ethoxy-2,3-dihydro- 3,3-dimethyl-5-benzofuranyl methanesulfonate;
  • diflufenican is the common name for 2'4'-difluoro- 2-( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyloxy) nicotinanilide;
  • tribenuron-methyl is the common name for methyl
  • mecoprop is the common name for (RS)-2-(4-chloro- 2-methylphenoxy)propionic acid
  • 2,4-D is the common name for 2-(4-chloro-2-methyl- phenoxy) acetic acid
  • benazolin-ethyl is the common name for ethyl (4-chloro- 2,3-dihydro-2-oxo-1,3-benzothiazol-3-yl) acetate;
  • dicamba is the common name for 3,6-dichloro-2-methoxy- benzoic acid
  • fluroxypyr is the common name for (4-amino-3,5-dichloro- 6-fluoro-2-pyridyloxy) acetic acid
  • guinmerac is the common name for 7-chloro-3-methyl- 8-quinollnecarboxyiate.
  • the combination of active ingredients of the invention can used for example against the following plant species:
  • the combinations can be applied pre or post-emergently, but generally pre-emergently. Selectivity is seen in range of crops such as maize, cereals and sunflowers.
  • the rate of use lies between 0.001 and 5 kg/ha of the mixture, depending on the use. By using the mixtures for control of weeds the amount of herbicide needed can be generally reduced.
  • the weight ratio of component a) to b) is generally
  • mixtures of the invention can also be used in
  • 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.
  • the designated active ingredients or their mixtures can suitably be used, for example, as powders, dusts,
  • liquid carriers are, for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide,
  • Suitable solid carriers include mineral earths, e.g.
  • 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 l/ha.
  • the agents can be applied using low-volume or ultra-low-volume techniques or in the form of so-called microgranules.
  • compositions can be carried out in known manner, for example by milling or mixing
  • individual components can be mixed just before use for example by the so-called commonly used tank-mixing method.
  • X the herbicidal activity (%) of substance A at a rate of p g/ha.
  • Y the herbicidal. activity (%) of substance B at a rate of q g/ha.
  • component I is 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo- [2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro- 4-(2-propynyl)-2H-1,4-benzoxazin-3 (4H) -onn

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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 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one and another selective herbicide.

Description

SYNERGISTIC HERBICIDAL COMPOSITIONS
This invention relates to a new herbicidal composition having synergistic activity comprising a mixture of
6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo- [2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro- 4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
and another selective herbicide and its use for combating weeds in crops.
The herbicidal activity of 6-(6,6-dimethyl- 3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol- 3-ylidenimino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin- 3(4H)-one is already known (EP 311 135). This compound has the following chemical structure (I)
(I)
Figure imgf000003_0001
Selective herbicides which inhibit directly or indirectly photosynthesis, demonstrate inhibition of cell division or possess hormone type activity are generally known. The known substances however are not always satisfactory in their activity in all areas of use.
It has now been found that a herbicidal composition which comprises, as active components, a mixture of
6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo-
[2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro- 4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one and anooher selective herbicide shows especially high activity without losing the selectivity properties in agricultural crops.
Surprisingly the herbicidal activity of the combination of the active ingredients of the invention is essentially higher than the individual components and also of the sum of the individual components. A synergistic effect is also seen. Especially suitable are mixtures which contain as a mixture component the selective herbicides cyanazine, ioxynil, isoproturon, methabenzthiazuron, bifenox,
chlorsulfuron, metsulfuron-methyl, pendimethalin,
benfuresate, thifensulfuron-methyl, isoxaben,
imazamethabenz, triasulfuron, amidosulfuron, ethofumesate, diflufenican, tribenuron-methyl, mecoprop, 2,4-D,
benazolin-ethyl, fluroxypyr or quinmerac.
Cyanazine is the common name for 2-chloro-4-(1-cyano- 1-methylethylamino)-6-ethylamino-1,3,5-triazine;
ioxynil is the common name for 4-hydroxy-3,5-diiodo- benzonitrile;
isoproturon is the common name for 3-(4-isopropylphenyl)- 1,1-dimethylurea;
methabenzthiazuron is the common name for 1-(benzothiazol- 2-yl)-1,3-dimethylurea;
bifenox is the common name for methyl 5-(2,4-dichloro- phenoxy)-2-benzoate;
chlorsulfuron is the common name for 1-(2-chlorophenyl- sulfonyl)-3-(4-methoxy-3-methyl-1,3,5-triazin-2-yl)urea; metsulfuron-methyl is the common name for methyl
2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino- carbonylaminosulfonyl]benzoate;
pendimethalin is the common name for N-(1-ethylpropyl)- 3,4-dimethyl-2,6-dinitroaniline; benfuresate is the common name for 2,3-dihydro- 3,3-dimethyl-5-benzofuranyl ethanesulfonate;
thifensulfuron-methyl is the common name for methyl
3-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino- carbonylaminosulfonyl]-2-thiophenecarboxylate;
isoxaben is the common name for N-[3-(1-ethyl-1-methyl- propyl)isoxazol-5-yl]-2,6-dimethoxybenzamide;
imazamethabenz is the common name for 2-[4-isopropyl- 4-methyl-5-oxo-2-imidazolin-2-yl)-4 (5) -methylbenzoate; triasulfuron is the common name for 1-(2-chlorethoxy)-
N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]- benzenesulfonamide;
amidosulfuron is the common name for 1-(4,6-dimethoxy- pyrimidin-2-yl)-3-(N-methyl-N-methylsulfonylsulfamoyl)- urea;
ethofumesate is the common name for 2-ethoxy-2,3-dihydro- 3,3-dimethyl-5-benzofuranyl methanesulfonate;
diflufenican is the common name for 2'4'-difluoro- 2-(α,α,α-trifluoro-m-tolyloxy) nicotinanilide;
tribenuron-methyl is the common name for methyl
2-[4-methoxy-6-methyl-1, 3 , 5-triazin-2-yl(methyl)- carbamoylsulfamoyl]benzoate;
mecoprop is the common name for (RS)-2-(4-chloro- 2-methylphenoxy)propionic acid;
2,4-D is the common name for 2-(4-chloro-2-methyl- phenoxy) acetic acid;
benazolin-ethyl is the common name for ethyl (4-chloro- 2,3-dihydro-2-oxo-1,3-benzothiazol-3-yl) acetate;
dicamba is the common name for 3,6-dichloro-2-methoxy- benzoic acid
fluroxypyr is the common name for (4-amino-3,5-dichloro- 6-fluoro-2-pyridyloxy) acetic acid; and
guinmerac is the common name for 7-chloro-3-methyl- 8-quinollnecarboxyiate. The combination of active ingredients of the invention can used for example against the following plant species:
Dicotyledonous weeds of the species Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga,
Chenopodium, Brassica, Urtica, Senecio, Amaranthus,
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola,
Galeopsis, Papaver, Centaurea and Chrysanthemum.
Monocotyledonous weeds of the species Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron,
Sagittaria, Monocharia, Fimbristylis, Eleocharis,
Ischaemum and Apera.
The combinations can be applied pre or post-emergently, but generally pre-emergently. Selectivity is seen in range of crops such as maize, cereals and sunflowers. The rate of use lies between 0.001 and 5 kg/ha of the mixture, depending on the use. By using the mixtures for control of weeds the amount of herbicide needed can be generally reduced.
The weight ratio of component a) to b) is generally
between 1:50 and 50:1.
The mixtures of the invention can also be used in
admixture with other active agents for example other plant-protection agents or pesticides.
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 l/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 tank-mixing method.
The following Examples illustrate the use of compositions of the invention.
The calculation of synergistic effect is carried out according to S R Colby "Calculating Synergistic and
Antagonistic Response to Herbicide Combinations" , Weeds, 15/1, 1967 pages 20 to 22. In this the following formula was used:
XY
E = X + Y - ------
100
in which X = the herbicidal activity (%) of substance A at a rate of p g/ha.
Y = the herbicidal. activity (%) of substance B at a rate of q g/ha., and
E = the expected additive activity of the
herbicide (%) of the substances A + B at a rate of p + q g/ha.
If the observed value is greater than the value of E calculated according to Colby, the combination shows synergistic activity. Experiments
In a greenhouse the plant species shown in the tables were treated pre-emergently with the components at the stated rates. The compositions were diluted with 500 litres of water and sprayed over the soil. Two weeks after treatment the herbicidal effect was evaluated. In the examples component I is 6-(6,6-dimethyl-3,5,6,7-tetrahydropyrrolo- [2,1-c][1,2,4]thiadiazol-3-ylidenimino)-7-fluoro- 4-(2-propynyl)-2H-1,4-benzoxazin-3 (4H) -onn
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Claims

Claims
1. A herbicidal composition which comprises, as active components, a mixture of 6-(6,6-dimethyl-
3,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]thiadiazol- 3-ylidenimino)-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin- 3(4H)-one and another selective herbicide.
2. A composition according to claim 1 which contains cyanazine, ioxynil, isoproturon, methabenzthiazuron, bifenox, chlorsulfuron, metsulfuron-methyl, pendimethalin, benfuresate, thifensulfuron-methyl, isoxaben,
imazamethabenz, triasulfuron, amidosulfuron, ethofumesate, diflufenican, tribenuron-methyl, mecoprop, 2,4-D,
benazolin-ethyl, fluroxypyr or quinmerac as the other selective herbicide.
3. A composition according to claims 1 or 2 in which the weight ratio of the mixture components is between 1:50 and 50:1.
4. A method of combating weeds which comprises applying post emergently a composition as claimed in any one of the preceding claims.
PCT/EP1992/002185 1991-09-23 1992-09-21 Synergistic herbicidal compositions Ceased WO1993005655A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP5505798A JPH06510775A (en) 1991-09-23 1992-09-21 Synergistic herbicide composition
FI941330A FI941330A0 (en) 1991-09-23 1992-09-21 Synergistic herbicidal compositions
EP92919951A EP0605533A1 (en) 1991-09-23 1992-09-21 Synergistic herbicidal compositions
AU25891/92A AU652481B2 (en) 1991-09-23 1992-09-21 Synergistic herbicidal compositions
BR9206527A BR9206527A (en) 1991-09-23 1992-09-21 Synergistic herbicidal compositions
SK336-94A SK33694A3 (en) 1991-09-23 1992-09-21 Synergistic herbicidal composition and the method of weed destruction
BG98672A BG98672A (en) 1991-09-23 1994-03-21 SYNERGITIC HERBICIDAL COMPOSITIONS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4132089A DE4132089A1 (en) 1991-09-23 1991-09-23 HERBICIDES WITH SYNERGISTIC EFFECT
DEP4132089.1 1991-09-23

Publications (1)

Publication Number Publication Date
WO1993005655A1 true WO1993005655A1 (en) 1993-04-01

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PCT/EP1992/002185 Ceased WO1993005655A1 (en) 1991-09-23 1992-09-21 Synergistic herbicidal compositions

Country Status (21)

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EP (1) EP0605533A1 (en)
JP (1) JPH06510775A (en)
CN (1) CN1071048A (en)
AU (1) AU652481B2 (en)
BG (1) BG98672A (en)
BR (1) BR9206527A (en)
CA (1) CA2119655A1 (en)
CZ (1) CZ68094A3 (en)
DE (1) DE4132089A1 (en)
FI (1) FI941330A0 (en)
HU (1) HUT67942A (en)
IL (1) IL102870A0 (en)
MA (1) MA22653A1 (en)
MX (1) MX9205362A (en)
PT (1) PT100886A (en)
SK (1) SK33694A3 (en)
TR (1) TR26286A (en)
WO (1) WO1993005655A1 (en)
YU (1) YU86292A (en)
ZA (1) ZA927278B (en)
ZW (1) ZW14892A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994018836A1 (en) * 1993-02-17 1994-09-01 Schering Aktiengesellschaft Synergistic herbicidal composition on the basis of thidiazimin
US5748396A (en) * 1995-11-13 1998-05-05 Seagate Technology, Inc. Arrangement and method for optimizing the recorded signal to noise ratio in contact recording systems
WO2003055310A1 (en) * 2001-12-25 2003-07-10 Nihon Nohyaku Co., Ltd. Herbicidal compositions and method of using the same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106386813B (en) * 2016-08-31 2018-10-16 四川利尔作物科学有限公司 Herbicidal combinations and its application

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2163427A (en) * 1984-08-08 1986-02-26 Nippon Soda Co Herbicidal thia (oxa) diazole derivatives
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2163427A (en) * 1984-08-08 1986-02-26 Nippon Soda Co Herbicidal thia (oxa) diazole derivatives
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

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 8948, 31 January 1990 Derwent Publications Ltd., London, GB; Class C, AN 89-351371/48 & JP,A,1 261 310 (SUMITOMO CHEM IND) 13 October 1989 *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 9011, 9 May 1990 Derwent Publications Ltd., London, GB; Class C, AN 90-079173/11 & JP,A,2 032 004 (SUMITOMO CHEM IND) 1 February 1990 *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 9011, 9 May 1990 Derwent Publications Ltd., London, GB; Class C, AN 90-079174/11 & JP,A,2 032 005 (SUMITOMO CHEM IND) 1 February 1990 *
CHEMICAL PATENTS INDEX, DOCUMENTATION ABSTRACTS JOURNAL Section Ch, Week 9013, 23 May 1990 Derwent Publications Ltd., London, GB; Class C, AN 90-094543/13 & JP,A,2 045 404 (SUMITOMO CHEM IND) 15 February 1990 *
WEED ABSTRACTS vol. 35, no. 5, May 1986, SLOUGH, GB N.N. 'List of common names and abreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts' *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994018836A1 (en) * 1993-02-17 1994-09-01 Schering Aktiengesellschaft Synergistic herbicidal composition on the basis of thidiazimin
US5748396A (en) * 1995-11-13 1998-05-05 Seagate Technology, Inc. Arrangement and method for optimizing the recorded signal to noise ratio in contact recording systems
WO2003055310A1 (en) * 2001-12-25 2003-07-10 Nihon Nohyaku Co., Ltd. Herbicidal compositions and method of using the same

Also Published As

Publication number Publication date
ZW14892A1 (en) 1993-05-12
FI941330L (en) 1994-03-22
PT100886A (en) 1994-01-31
YU86292A (en) 1995-10-03
HUT67942A (en) 1995-05-29
SK33694A3 (en) 1994-08-10
BG98672A (en) 1995-05-31
ZA927278B (en) 1993-03-22
CN1071048A (en) 1993-04-21
MX9205362A (en) 1993-05-01
TR26286A (en) 1995-02-15
FI941330A7 (en) 1994-03-22
AU652481B2 (en) 1994-08-25
EP0605533A1 (en) 1994-07-13
CZ68094A3 (en) 1994-12-15
BR9206527A (en) 1995-11-07
IL102870A0 (en) 1993-01-31
CA2119655A1 (en) 1993-04-01
MA22653A1 (en) 1993-04-01
AU2589192A (en) 1993-04-27
FI941330A0 (en) 1994-03-22
HU9400825D0 (en) 1994-06-28
DE4132089A1 (en) 1993-03-25
JPH06510775A (en) 1994-12-01

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