DE2104233A1 - Unkrautbekämpfungsmittel - Google Patents
UnkrautbekämpfungsmittelInfo
- Publication number
- DE2104233A1 DE2104233A1 DE19712104233 DE2104233A DE2104233A1 DE 2104233 A1 DE2104233 A1 DE 2104233A1 DE 19712104233 DE19712104233 DE 19712104233 DE 2104233 A DE2104233 A DE 2104233A DE 2104233 A1 DE2104233 A1 DE 2104233A1
- Authority
- DE
- Germany
- Prior art keywords
- triazine
- chloro
- cyclopropylamino
- methoxy
- tert
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title description 9
- 241000196324 Embryophyta Species 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 2-chloro-4- (1-methoxy-2-propylamino) -6-cyclopropylamino- s-triazine Chemical compound 0.000 claims description 11
- 229920000742 Cotton Polymers 0.000 claims description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 235000020232 peanut Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- BFZPFVIKDQXXKY-UHFFFAOYSA-N 4,6-dichloro-n-cyclopropyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC2CC2)=N1 BFZPFVIKDQXXKY-UHFFFAOYSA-N 0.000 claims description 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
- 235000018262 Arachis monticola Nutrition 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- OOHIAOSLOGDBCE-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC(Cl)=NC(NC2CC2)=N1 OOHIAOSLOGDBCE-UHFFFAOYSA-N 0.000 claims 1
- 241001553178 Arachis glabrata Species 0.000 claims 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 244000299507 Gossypium hirsutum Species 0.000 description 6
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 244000105624 Arachis hypogaea Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 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
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KALSOJKUICKBCX-UHFFFAOYSA-N 2-n-propylpyrimidine-2,4-diamine Chemical compound CCCNC1=NC=CC(N)=N1 KALSOJKUICKBCX-UHFFFAOYSA-N 0.000 description 1
- JWWJNBZOZURGQN-UHFFFAOYSA-N 4-n-cyclopropyl-6-methoxy-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC(NC(C)C)=NC(NC2CC2)=N1 JWWJNBZOZURGQN-UHFFFAOYSA-N 0.000 description 1
- KQXDRJBWTCCQFU-UHFFFAOYSA-N 6-chloro-2-n-cyclopropyl-4-n-propyl-1,3,5-triazine-2,4-diamine Chemical compound CCCNC1=NC(Cl)=NC(NC2CC2)=N1 KQXDRJBWTCCQFU-UHFFFAOYSA-N 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 241000561734 Celosia cristata Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- PFVKYIGBPAAFOC-UHFFFAOYSA-N n-cyclopropyl-1,3,5-triazin-2-amine Chemical compound C1CC1NC1=NC=NC=N1 PFVKYIGBPAAFOC-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920006327 polystyrene foam Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US807870A | 1970-02-02 | 1970-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2104233A1 true DE2104233A1 (de) | 1972-03-16 |
Family
ID=21729687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712104233 Pending DE2104233A1 (de) | 1970-02-02 | 1971-01-29 | Unkrautbekämpfungsmittel |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH530758A (https=) |
| DE (1) | DE2104233A1 (https=) |
| FR (1) | FR2077996A5 (https=) |
| GB (1) | GB1313264A (https=) |
| TR (1) | TR17437A (https=) |
-
1971
- 1971-01-29 DE DE19712104233 patent/DE2104233A1/de active Pending
- 1971-02-01 TR TR1743771A patent/TR17437A/xx unknown
- 1971-02-01 FR FR7103204A patent/FR2077996A5/fr not_active Expired
- 1971-02-01 CH CH143571A patent/CH530758A/fr not_active IP Right Cessation
- 1971-04-19 GB GB2096171A patent/GB1313264A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2077996A5 (https=) | 1971-11-05 |
| CH530758A (fr) | 1972-11-30 |
| GB1313264A (en) | 1973-04-11 |
| TR17437A (tr) | 1975-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |