DE3045770C2 - - Google Patents
Info
- Publication number
- DE3045770C2 DE3045770C2 DE3045770A DE3045770A DE3045770C2 DE 3045770 C2 DE3045770 C2 DE 3045770C2 DE 3045770 A DE3045770 A DE 3045770A DE 3045770 A DE3045770 A DE 3045770A DE 3045770 C2 DE3045770 C2 DE 3045770C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- emergence
- weeds
- methyl
- dimethylurea
- 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.)
- Expired
Links
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- 239000004480 active ingredient Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- BNRXAOCOHIHDTC-UHFFFAOYSA-N 1,1-dimethyl-3-(3-methyl-4-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1C BNRXAOCOHIHDTC-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 30
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MKYJJJUJQHKWNM-UHFFFAOYSA-N 3-methyl-4-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(N)C=C1C MKYJJJUJQHKWNM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 244000025254 Cannabis sativa Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 240000006503 Lamium purpureum Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000005324 Typha latifolia Nutrition 0.000 description 3
- 241000990144 Veronica persica Species 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
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- 238000001228 spectrum Methods 0.000 description 3
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- 239000004546 suspension concentrate Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 235000012587 Lamium purpureum var. incisum Nutrition 0.000 description 2
- 244000100545 Lolium multiflorum Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 235000017945 Matricaria Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000006928 Persicaria lapathifolia Species 0.000 description 2
- 244000292693 Poa annua Species 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 240000000260 Typha latifolia Species 0.000 description 2
- 241001148683 Zostera marina Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
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- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 2
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- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
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- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942224 | 1979-12-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3045770A1 DE3045770A1 (de) | 1981-10-15 |
| DE3045770C2 true DE3045770C2 (enrdf_load_stackoverflow) | 1989-04-20 |
Family
ID=10509686
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803045770 Granted DE3045770A1 (de) | 1979-12-06 | 1980-12-04 | Harnstoff-derivat, verfahren zu seiner herstellung und herbizide mittel die dieses enthalten |
| DE19803045785 Withdrawn DE3045785A1 (de) | 1979-12-06 | 1980-12-04 | 2,5-dialkylphenalharnstoff-derivate, verfahren zu ihrer herstellung und herbizide mittel, die diese substanzen enthalten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803045785 Withdrawn DE3045785A1 (de) | 1979-12-06 | 1980-12-04 | 2,5-dialkylphenalharnstoff-derivate, verfahren zu ihrer herstellung und herbizide mittel, die diese substanzen enthalten |
Country Status (30)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2577221B1 (fr) * | 1985-02-11 | 1987-02-20 | Rhone Poulenc Agrochimie | Procede de preparation d'une phenyluree substituee |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655447A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | Composition and method |
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| IL31574A0 (en) * | 1968-02-13 | 1969-04-30 | Ciba Ltd | Use of certain ureas for combating weeds |
| US3649241A (en) * | 1969-07-22 | 1972-03-14 | Du Pont | 1-(p-cumyl)-3,3-dimethylureas as selective herbicide |
-
1980
- 1980-11-04 CA CA000363944A patent/CA1201725A/en not_active Expired
- 1980-11-25 CU CU8035374A patent/CU35374A/es unknown
- 1980-11-27 BE BE1/10053A patent/BE886365A/nl not_active IP Right Cessation
- 1980-11-27 BE BE1/10052A patent/BE886364A/nl not_active IP Right Cessation
- 1980-12-03 EG EG749/80A patent/EG14536A/xx active
- 1980-12-03 NL NL8006569A patent/NL8006569A/nl not_active Application Discontinuation
- 1980-12-03 NL NL8006568A patent/NL8006568A/nl not_active Application Discontinuation
- 1980-12-04 DE DE19803045770 patent/DE3045770A1/de active Granted
- 1980-12-04 FR FR8025795A patent/FR2471371A1/fr active Granted
- 1980-12-04 OA OA57267A patent/OA06709A/xx unknown
- 1980-12-04 IT IT8026436A patent/IT8026436A0/it unknown
- 1980-12-04 DK DK519480A patent/DK154502C/da not_active IP Right Cessation
- 1980-12-04 IT IT26437/80A patent/IT1141111B/it active
- 1980-12-04 BR BR8007953A patent/BR8007953A/pt not_active IP Right Cessation
- 1980-12-04 GB GB8038889A patent/GB2066814B/en not_active Expired
- 1980-12-04 PT PT72156A patent/PT72156B/pt unknown
- 1980-12-04 TR TR20936A patent/TR20936A/xx unknown
- 1980-12-04 DD DD80225710A patent/DD154955A5/de unknown
- 1980-12-04 DE DE19803045785 patent/DE3045785A1/de not_active Withdrawn
- 1980-12-04 CH CH895980A patent/CH645347A5/de not_active IP Right Cessation
- 1980-12-04 DD DD80225709A patent/DD154956A5/de unknown
- 1980-12-04 JP JP17032280A patent/JPS5692258A/ja active Granted
- 1980-12-04 PL PL1980232826A patent/PL127924B1/pl unknown
- 1980-12-04 ES ES497434A patent/ES8200652A1/es not_active Expired
- 1980-12-04 AT AT0592780A patent/AT381006B/de not_active IP Right Cessation
- 1980-12-04 PL PL1980228264A patent/PL125931B1/pl unknown
- 1980-12-04 CH CH895880A patent/CH645346A5/de not_active IP Right Cessation
- 1980-12-04 YU YU03076/80A patent/YU307680A/xx unknown
- 1980-12-04 HU HU802901A patent/HU185226B/hu not_active IP Right Cessation
- 1980-12-04 ZA ZA00807581A patent/ZA807581B/xx unknown
- 1980-12-04 ZA ZA00807582A patent/ZA807582B/xx unknown
- 1980-12-04 BG BG049871A patent/BG33431A3/xx unknown
- 1980-12-04 SE SE8008535A patent/SE8008535L/ not_active Application Discontinuation
- 1980-12-04 AU AU65058/80A patent/AU540420B2/en not_active Ceased
- 1980-12-04 PL PL1980228263A patent/PL125992B1/pl unknown
- 1980-12-04 JP JP17032380A patent/JPS5692259A/ja active Pending
- 1980-12-04 ES ES497435A patent/ES8200650A1/es not_active Expired
- 1980-12-04 DK DK519580A patent/DK519580A/da not_active Application Discontinuation
- 1980-12-04 YU YU03081/80A patent/YU308180A/xx unknown
- 1980-12-04 IL IL61629A patent/IL61629A0/xx unknown
- 1980-12-04 SE SE8008536A patent/SE8008536L/ not_active Application Discontinuation
- 1980-12-04 NZ NZ195760A patent/NZ195760A/xx unknown
- 1980-12-04 AU AU65059/80A patent/AU6505980A/en not_active Abandoned
- 1980-12-04 FR FR8025793A patent/FR2471370A1/fr active Granted
- 1980-12-04 IL IL61628A patent/IL61628A0/xx unknown
- 1980-12-04 BR BR8007954A patent/BR8007954A/pt unknown
- 1980-12-05 PH PH24957A patent/PH16412A/en unknown
-
1984
- 1984-05-31 KE KE3410A patent/KE3410A/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |