IE832899L - Herbicide containing dinitroaniline and urea derivatives - Google Patents
Herbicide containing dinitroaniline and urea derivativesInfo
- Publication number
- IE832899L IE832899L IE289983A IE289983A IE832899L IE 832899 L IE832899 L IE 832899L IE 289983 A IE289983 A IE 289983A IE 289983 A IE289983 A IE 289983A IE 832899 L IE832899 L IE 832899L
- Authority
- IE
- Ireland
- Prior art keywords
- aqueous emulsion
- concentrate
- emulslfiable
- alkyl
- general formula
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 9
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 title 1
- 150000003672 ureas Chemical class 0.000 title 1
- 239000000839 emulsion Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000012141 concentrate Substances 0.000 claims description 12
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims description 11
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 11
- 239000005573 Linuron Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 6
- 239000003849 aromatic solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- -1 urea compound Chemical class 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 230000000052 comparative effect Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 claims description 2
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 2
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical class CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- 239000005471 Benfluralin Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1.
HERBICIDAL COMPOSITIONS COMTAIHIWG DIHITROANILIWE AND UREA DERIVATIVES This Invention relates to herbicide compositions comprising a dinltroanillne such as trifluralln and a urea herbicide such as linuron.
It has been known to supply these chemicals to 5. the farmer or other user as an emulsifiable concentrate but the choice of a solvent for the concentrate has presented difficulties. Whereas dinltroanilines such as trifluralln tend to dissolve readily in common aromatic solvents, urea components 10. such as linuron are not so easily dissolved. it has been proposed to use a mixture of dimethyl foraamide and xylene as a solvent for trifluralln and linuron, but it has been found that whan working emulsions have been prepared from an emulsifiable 15. concentrate comprising such a mixture, crystalline precipitates tend to form if the working emulsion is left for periods of time, such as overnight. In particularly bad cases, such precipitates can block nozzles of a spraying machine. Xn any case, the pre-20. cipitate will tend to settle at the bottom of, for example, the tank of a spraying machine and so the concentration of herbicide applied by the spraying machine will be reduced, thereby leading to less effective weed control.
It has now been found that ethyl amyl ketone can be used as a solvent for dinltroanillne herbicides and urea herbicides. A composition of a dinltroanillne * 2. herbicide, a urea herbicide and ethyl amyl ketone has been found not to cause a crystalline precipitate to be deposited for 24 hours.
According to a first aspect of the present Invention, there is provided an emulslfiable con-5t centrate or aqueous emulsion comprising a dinltroanillne compound of general formula U), *l y -HO 10. c,j 2 (X) in which R1 and R2 are the same or different and each 15. represents alkyl or alkenyl, a urea compound of general formula (II), 'A 20. R - **cc\ 4 (IX) in which R3 and R* are the same or different and each represents Cj_4 alkyl or Cj_4 alkoxy and R* represents hydrogen or up to five substituents each selected from 25. cl-4 ' cl-4 alko*y and halogen, and ethyl amyl ketone.
Xn general formula (X), R1 preferably represents 2 C2_3 alkyl and R preferably represents Cj ^ alkyl or C4 alkenyl. Xn general formula (XX), R^ preferably 30. represents a substituent in the 3 and/or 4 position.
Particularly preferred compounds of general formula (X) are benfluralin, trifluralln and ethal-fluralin, trifluralln being especially preferred. 3.
Particularly preferred compounds of general formula (II) are metoxuron, chlortoluron, isoproturon, linuron and neburon, linuron being especially preferred.
While compositions according to the invention nay comprise one compound of general formula (I) and one compound of general formula (II) the Invention also encompasses compositions having more than one compound of one or both general formulae.
In preferred compositions, the weight ratio lO. of the amount of compound (s) of formula (II) to the amount of ocmpound (s)of formula (I) is from 1:1 to 1:5, for example from 1:1 to 1:4, preferably from 1:1.25 to 1:3, particularly preferably 1:1.5 to 1:2.5. Typical such ratios are 1:2.1 and 1:2.3. 15. Compositions in accordance with the invention may also comprise other ingredients such as emulsifiers and aromatic solvents compatible with ethyl amyl ketone. Preferred emulsifiers Include anionic and non-ionic surfactants. Alkyl aryl ethoxylates and alkali 20. metal and alkaline earth salts of alkyl aryl sulphonic acids are particularly preferred. One or more emulsifiers may be present.
Aromatic solvents compatible with ethyl amyl ketone Include xylene, heavy aromatic naphthas, mixtures 25. of alkyl benzene compounds and o-chlorotoluenes. One or more of such compounds may be present.
The present invention extends in a preferred aspect to an emulslfiable concentrate or aqueous emulsion comprising trifluralln, linuron, ethyl amyl 30. keto**«» an emulsifler and an aromatic solvent compatible with ethyl aayl ketone.
Compositions in accordance with the first 4. aspect of tha Invention auty be emulslfiable concentrates Which, can be nixed, at concentrations of 1.22 - 10.0% with water to form a working emulsion.
An aqueous emulsion in accordance with the invention 5. may be applied directly to agricultural land by the. farmer to control or eliminate weeds.
According to a second aspect of the present invention there is therefore provided a method of controlling or eliminating weeds in an area of land, 10. which, method comprises applying to the area an aqueous emulsion In accordance with the first aspect.
To illustrate the present Invention the following examples will new be given: goumuB 1 A composition was prepared from the following ingredients in the proportions indicated.
Ingredient Linuron Trifluralln BP A180 Ethyl amyl ketone Burteaul'Sl Burtemul >14 100% % w/r 12.0 24.0 24.0 (1) 30.0 5.1 (2) 4.9 (3) MOTES: (1) BP A180 Is an aromatic hydrocarbon solvent. (2) Burtemul SI is an emulslfier and contains 70% calcium dodecyl benzene sulphonate and 30% butanol. (3) Burtemul M14 is an emulslfier and is nonyl phenol 14 mole ethylene oxide..
* Burtemul is.a Trade Hark 6.
The composition was nixed with 40 volumes of water. 200 litres of the resulting aqueous emulsion was used to treat 1 hectare of land in which winter cereals were growing. The treatment was carried out prior to crop 5. emergence.There was no damage to the crop and the weed control was 89%.
EXAMPLES 2 to 5 Compositions were prepared from the following 10. ingredients in the proportions Indicated : EXAMPLE NO. 2 3 % w/v 4 5 Linuron (100%) 15 12.5 10 7.5 Trifluralln (1001) 15 17.5 20 22.5 Ethyl arayl ketone 45 38 30 25 Alkyl aryl ethcocylate and) alkali metal salt of an ) (1) alkyl aryl sulphonic acid) 10 10 10 10 Axcmstic solvent to 100% volume 25.
NOTE: (1) emulslfier A 2.5% dilution in water of each of the compositions 30. of Examples 4 and 5 was prepared and kept at a temperature of 20°C. The dilutions were examined after 7. 12 and 24 hours and no precipitate was observed after these tines in either case.
COMPARATIVE EXAMPLES 1 and 2 Compositions containing dimethyl form amide but no ethyl amyl ketone were prepared from the following ingredients in the proportions indicated i 10.
COMPARATIVE EXAMPLE MO. % w/v 1 2 15. 20.
Linuron (100%) Trtfluralin (100%) Dimethyl frffUMirlrte Bacol N 30CB + ) Bacol N 500C Xylene MOTE* (1) emulslfier ) (1) 10 20 15 8 to 100% volume 7.5 22.5 12 8 A 2.5% dilution in water of each of the compositions 25. of Comparative Examples 1 and 2 was prepared and kept at a temperature of 20°C. The dilutions were examined after 12 hours and in each case a crystalline precipitate was seen to have formed. 8.
Claims (13)
1. CLAIMS : X. An emulslfiable concentrate or aqueous emulsion comprising a dinltroanillne compound of general formula IX) R* R2 5. 02*v (X) 1Q in Which R1 and X2 are the same or different and each represents Cj_4 alkyl or C2_4 alkenyl, a urea compound of general formula (II), .3 (IX) 20. 15. r'A * in which R3 and R4 are the same or different and each represents Cj_4 alkyl or Cj,_4 alkoxy and RA represents hydrogen or up to five substituents each selected from Cj_4 alkyl, C1-4 alkoxy and halogen, and ethyl amyl ketone.
2. An emulslfiable concentrate or aqueous emulsion as claimed in Claim 1 wherein, in general formula (1), R1 represents C2_3 alkyl and R2 represents C3_4 alkyl or C4 alkenyl. 25.
3. * An emulslfiable concentrate or aqueous emulsion as claimed in Claim 1 or 2, wherein, in general formula (II), K* represents a substituent in the 3 and/or 4 position. 9.
4. An emulslfiable concentrate or aqueous emulsion as claimed in Claim 1, 2 or 3 wherein the compound of general formula (I) is benfluralln, trifluralln or ethalfluralin. 5.
5. An emulslfiable concentrate or aqueous emulsion as claimed in any one of Claims 1 to 4, wherein the compound of formula (IX) is metoxuron# chlortoluron, isoproturon, linuron or neburon. 10.
6. An emulslfiable concentrate or aqueous emulsion as claimed in any one of Claims 1 to 5, wherein the weight ratio of the amount of compound(s) of formula (II) to the amount of compounds(s) of 15. formula (I) is from 1:1.5 to 1:2.5.
7. An emulslfiable concentrate or aqueous emulsion as claimed in any one of Claims 1 to 6, including an aromatic solvent compatible with 20. ethyl amyl ketone.
8. An emulslfiable concentrate or aqueous emulsion comprising trifluralln, linuron, ethyl amyl ketone, an emulslfier and an aromatic solvent 25. Compatible with ethyl amyl ketone.
9. A method of controlling or eliminating weeds in an area of land, which method comprises applying to the area an aqueous emulsion as claimed 30. in any one of Claims 1 to 8.
10. A composition substantially as described in any one of Examples 1 to 5. xo.
11. An aqueous emulsion including a composition substantially as described in any one of Examples 1 to 5.
12. 5. 12. A method of controlling or eliminating weeds in an area of land, which method comprises applying to the area an aqueous emulsion as claimed in Claim 11.
13. A herbicide composition, or an aqueous 10. emulsion thereof, substantially as herein described in any of Examples 1 to 5 (but not including Comparative Examples 1 and 2). MACLACHLAN ft DONALDSON Applicahts' Agents, 47 Merrion Square, DUBLIN 2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8235235 | 1982-12-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE832899L true IE832899L (en) | 1984-06-10 |
| IE56367B1 IE56367B1 (en) | 1991-07-03 |
Family
ID=10534873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE289983A IE56367B1 (en) | 1982-12-10 | 1983-12-09 | Herbicidal compositions containing dinitroaniline and urea derivatives |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IE56367B1 (en) |
-
1983
- 1983-12-09 IE IE289983A patent/IE56367B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE56367B1 (en) | 1991-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |