IL31140A - Triazine derivatives - Google Patents
Triazine derivativesInfo
- Publication number
- IL31140A IL31140A IL31140A IL3114068A IL31140A IL 31140 A IL31140 A IL 31140A IL 31140 A IL31140 A IL 31140A IL 3114068 A IL3114068 A IL 3114068A IL 31140 A IL31140 A IL 31140A
- Authority
- IL
- Israel
- Prior art keywords
- triazine
- chloro
- amino
- per hectare
- wheat
- Prior art date
Links
- 150000003918 triazines Chemical class 0.000 title description 2
- 244000292693 Poa annua Species 0.000 description 20
- 240000006694 Stellaria media Species 0.000 description 20
- 241001621841 Alopecurus myosuroides Species 0.000 description 18
- 240000005979 Hordeum vulgare Species 0.000 description 18
- 240000008042 Zea mays Species 0.000 description 18
- 244000042664 Matricaria chamomilla Species 0.000 description 17
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 17
- 235000007340 Hordeum vulgare Nutrition 0.000 description 16
- 244000274883 Urtica dioica Species 0.000 description 15
- 235000009108 Urtica dioica Nutrition 0.000 description 15
- 241000209140 Triticum Species 0.000 description 14
- 244000024671 Brassica kaber Species 0.000 description 13
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 13
- 240000006122 Chenopodium album Species 0.000 description 13
- 235000021307 Triticum Nutrition 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 230000006378 damage Effects 0.000 description 9
- 235000011292 Brassica rapa Nutrition 0.000 description 8
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 8
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 8
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 8
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 8
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- 244000098338 Triticum aestivum Species 0.000 description 8
- 235000007244 Zea mays Nutrition 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 235000008427 Brassica arvensis Nutrition 0.000 description 5
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 241000219873 Vicia Species 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- 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
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
TRIAZINE DERIVATIVES BADISCHE ANILIN- & SODA-PABRIK A TIENOESELLSCHAPT 31140/3 '"Further active ingredients are named in the Examples.
As herbicides, the new compounds may be applied as solutions, , emulsions, suspensions or dusts. The form of application depends: ·■· entirel'y on the purpose for which the compounds are being used; in * any case, it should ensure a fine distribution' of the aotiye in-gredient . · > ' ' , For the preparation of solutions to be sprayed direct, mineral '. oil fractions having medium to high boiling points, such as kerosene or diesel oil, coal-tar., oils and oils of vegetable, or mineral Origin, and also cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes are suitable.; Aqueous, formulations may be prepared from1 emulsion concentrates,' pastes or 'wettable powders by adding water. To prepare emulsions, the ingredients as such or'dissolved in a solvent may be homogenized in water by means of wetting or dispersing agents (e.g. polyethylene ; oxide adducts). doncentrates which are suitable for' dilution witin : ; I ■■ ■■· ■· . ■ ■ . . ■ . .. ■ . · ; ■.. : . · . :f. ■" ■ ·,■ ■■■ water may be prepared from active ingredient, emulsifying or die-'.;, persing agent and possibly solvent.,, . '„ ', „, ' ,.·■ .■■■ ■ .■ . .,'.,_ ___^_J . . , \ .' Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier, e. g. clay, diatomite or fertilizers.
The following Examples demonstrate the superiority of the compositions according to this invention over known active ingredients.
EXAMPLE 1 Plastic pots having a diameter of 8 cm are filled with loamy sandy soil in a greenhouse and sown with seeds of taarley (Hordeum vulgare), wheat (Triticum sativum), Indian corn (Zea mays), annual meadow grass (Poa annua), slender foxtail (Alopecurus myosuroides), small nettle (Urtica urens), wild mustard (Sinapis arvensis), white goosefoot (Chenopodium album), vetch (Vicia sp.), chamomile (Matricaria chamomilla) and chickweed (Stellaria media); the soil prepared in this manner is then treated with 1.5 kg per hectare of 2-chloro-4-ethylamino-6- (< -methyl-S-methoxyethyl)-amino-l,3j 5-triazine (I) and, for comparison, with 1.5 kg per hectare of 2-chloro-4, 6-bis- (ethyl-amino)-s-triazine (il), these amounts of the active ingredients each being dispersed in 500 liters of water. After to 5 weeks I shows superior compatibility with barley (Hordeum vulgare) and wheat (Triticum sativum) and also exhibits a stronger herbicidal action on weeds.
The results of the experiment may be seen from the following table: Active ingredient I II barley 10 20-30 wheat 10 20 Indian corn 0-10 0-10 annual meadow grass 90 80 slender foxtail 80 70 small nettle 100 90-100 . . , Active ingredient I II vetch 90-100 80 chamomile 90 80-90 chickweed 90-100 8Ο-9Ο 0 = no damage 100 = total destruction EXAMPLE 2 In a greenhouse the plants barley (Hordeum vulgare), wheat (Triticum sativum), Indian corn (Zea mays), wild mustard (Sinapis arvensis), small nettle (Urtica urens), white goosefoot (Chenopodium album), chamomile (Matricaria chamomilla), chickweed (Stellaria media), annual meadow grass (Poa annua) and slender foxtail (Alo-pecurus myosuroides) are treated at a growth height of from J to 17 cm with 1.5 kg per hectare of the active ingredient 2-chloro-4-ethylamino-6- (tfC-methyl-B-methoxyethyl)-amino-l, > 5-triazine (i) and, for comparison, with 1.5 kg per hectare of the active ingredient 2-chloro-4,6-bis- (ethylamino)-s-triazine (il), each amount of the active ingredients being dispersed in 500 liters of water. After weeks it is ascertained that I shows superior compatibility with barley (Hordeum vulgare) and wheat (Triticum sativum) and also exhibits a stronger herbicidal effect on weeds.
The results of the experiment may be seen from the following table : Active ingredient I II barley 0-10 20-30 wheat 10 20-30 Indian corn 0 0-10 wild mustard 100 90-100 small nettle 90-100 90-100 - - O.Z. 25,248 Active ingredient I II annual meadow grass 90-100 90 slender foxtail 90 80 0 = no damage 100 = total destruction EXAMPLE 3 s In a greenhouse, seeds of wild mustard (Sinap'is arvensis), small nettle (Urtica' urens ) , white goosefoot (Chenopodium album), chamomile (Matricaria chamomilla), chickweed (Stellaria .media ) , annual meadow grass (Poa annua) and slender foxtail (Alopecurus myosuroides) are sown in loamy sandy soil; the soil prepared in this manner is then treated with 5kg per hectare of 2-chloro-4-ethylamino-6- (c£-methyl-B-methoxyethyl)-amino-l, 3, 5-triazine (I) and, for comparison, with kg per hectare of 2-chloro-4, 6-bis- (ethylamino)-1, 3, 5-triazine (II), each amount of the active ingredients being dispersed in 500 liters of water per hectare. After 4 to 5 weeks it is ascertained that I has a stronger herbicidal action than II.
EXAMPLE 4 The plants wild mustard (Sinapis arvensis), small nettle (Urtica urens), white goosefoot (Chenopodium album), chamomile (Matricaria chamomilla), chickweed (Stellaria media), annual meadow grass (Poa annua) and slender foxtail (Alopecurus myosuroides), growing on an experimental area, are treated at a growth height of 3 to 12 cm with 5kg per hectare of 2-chloro-4-ethylamino-6- (c£-methyl-8-methoxyethyl ) -amino-1,3, 5-triazine (I) and, for comparison, with 5kg per hectare of 2-chloro-4,6-bis-(ethylamino)-l,3, 5-triazine (II), these amounts of the active ingredients each being dispersed in 500 liters of water per hectare. After 1 to 2 weeks it is ascertained that I acts more quickly on the above-mentioned weeds and weed grasses than II, and in Examples 1, 2, 3 and 4i 2-chloro-4-isopropylaminO-6- (a-methyl-3-methoxyethyl)~amino-1,3,5 triazine, 2-chloro~4-tertlary-butylamino-6- (a-methyl- -methoxyetbyl)-amino-1,3,5-triazine, 2-chloro-4,6-bis- (a-methyΙ-β-aethox ethyl)-amino-1,3,5-triazine, 2-chloro-4-methylamino-6-(a-methyl-3-methoxyethyl)-amino-l,3 , 5-trlazine, 2-bromO-4-ethylamino-6-(a-methyl-P-methoxyethyl)-amino-l,3,5-triazine, 2-chloro-4-methoxyethylamino-6-(a-methyl-P-methoxyethyl)-amino-l,3,5«*triazine, 2-chloro-4-Y-methoxypropylamino-6 (a-methyl-P-methoxyethyl)-amlno-1,3 , 5-triazine,f EXAMPLE 5 Loamy sandy soil is filled into pots and sown with seeds of Indian corn (Zea mays), barley (Hordeum vulgare), wheat (Triticunv sativum), annual meadow grass (Poa annua), slender foxtail (Alo- I. ■pecurus myosuroides), white goosefoot (Chenopodlum album), small ' nettle (Urtica urens), wild mustard-(Sinapis aryensis), vetc .
(Vicia sp. ), chamomile (Matricaria champmilla) and chickweed (Stellaria media)';' the soil is then treated with 1.5kg per hectare of 2- chlor.o- Ί '' .· , 4-ethylamino-6-propoxyisopropylamino-s-triazine (I) 'and 1.5 kg per hectare of 2-chloro-4-isopropylamino-6-propoxyisopropylamirio-s-triazine (II), these amounts of the active ingredients each'being dispersed in 500 liters of water per hectare. The results of the experiment after to 5 weeks may be seen from the following Table: Active ingredient' ' Indian oorn . ^ 0-10. , 0-10. . barley ■ 10 ' 0-10 ..· wheat 10 · .. 0-10. ', annual meadow grass: 8Ο-9Ο 80 . · . · - i slender foxtail 80 80 small nettle 90-100 90-100 -.'wild mustard 100 90-100 white goosefoot i 90-100 90-100 .. vetch 90 . 80-90. chamomile . 90 80-90 chickweed 90-100 0 = no damage ' 100 = total' destruction O.Z. 25,248 EXAMPLE 6- In a greenhouse the plants barley (Hordeum vulgare), wheat (Triticum sativum), Indian corn (Zea mays), small nettle (Urtica urens) , .white goosefoot (Chenopodium album), chamomile (Matricaria chamomilla), chickweed (Stellaria media), annual meadow gras¾ (Poa annua), and slender foxtail (Alopecurus myosuroides) are treated at a growth height of 2.5 to 16 cm with 1.5kg per' hectare of 2-chloro-4-ethylamino-6-propoxyisopropylamino-s-triazine (I) and 1.5' kg per hectare of 2-chloro-4-isopropylamino-6-propoxyisopropyl-amino-s-triazine (II), these amounts of the active 'ingredients each be dispersed in 500 liters of water. The results of the experiment after 3 weeks may be seen from the following table :- . Active ingredient I II b'arley 10 0-10 wheat 0-10 0-10 ! Indian corn 10 0 small nettle •90-100 90-100 white goosefoot 90-100 90-100 chamomile 90-100 90-100 chickweed 100 ' 90-100 annual meadow grass .90-100 90-100 slender foxtail 90-100 90-100 0 = no damage 100 = to.tal destructi EXAMPLE 7 An experimental area is sown with wheat (Triticum sativum), barley (Hordeum vulgare), Indian corn (Zea mays), annual meadow grass (Poa annua), slender foxtail (Alopecurus myosuroides), barnyard millet (Echinocloa crus-galli), chickweed (Stellaria media) and chamomile (Matricaria chamomilla) . When the plants reached a height of 4-18 cm they were sprayed with 1 kg per hectare of the following active substances, dispersed or emulsified in 500 liters of water per hectare. After 2 to 3 weeks it could be observed that compounds I and II according to the invention are better tolerated by wheat, barley and Indian corn, as compared to the known compound III, while they exhibit a stronger herbicidal effect on weeds than compound III· Active substances: Compound I : 2-Ghloro-4-isopropylamino-6-(a-methyl-p-methoxy- ethyl)amino-l,3 , 5-triazine ; Compound II t 2-Chloro-4-ethylamino-6-(a-methyl«P-methoxy-ethyl)- amino-l,3,5-trlazinej and for comparison; Compound Hit 2-Chloro-4,6-di(Y-methoxy-propyl)amino-l,3,5«r triazlne (known) The main results of 6 experiments are shown in the following tablet I II III kg ha Active Substance 1 1 1 Triticum sativum 10 5 20 Hordeum vulgare 10 10 25 Zea mays 0 5,5 25 Poa annua 77,8 81,7 60,4 Alopecurus myosuroides 75,0 85,5 65,5 Echinochloa crus-galli 75 85,5 57 EXAMPLE 8 The herbicidal activity of the two known compoundsί Compound I: 2-Chloro-4-ethylamino-6-(Y-methoxy-propyl)amlno- 1,3,5-trlazine; and Compound 11» 2-Chl0ro-4-ieopropylamino-6-(Y-methoxy*propyl)- amino- ,3 , 5 rlazlne { was compared with the activity of the new compound according to the Invention« Compound III* 2~Chloro~4-ethylamino«6-(a-methyl-p-me hoxy- ethyl)amino-lf3, 5*»triazine ; in the following experiments t Experiment 1 Plastic pots having a diameter of 8 cm are filled with loamy sandy soil in a greenhouse and then sown with seeds of wheat (Trltlcum sativum), Indian corn (Zea mays), annual meadow grass (Poa annua), wild mustard (Sinapis arvensis), chickwe©¾ (Stellaria media) and barnyard millet (Echinocloa crus-galli) and the soil was thereafter treated with 1.5 kg per hectare of the active compounds I, II and III, dispersed with sodium lignine-sulfonate in 500 liters of water per hectare. After 4 to 5 weeks it is found tha active compound I exhibited only a weak herbicidal effect on the undesired weeds wild mustard, chickweed, annual meado grass and barnyard millet, while the active compound II caused severe damage to the culture plants wheat and Indian com. Only the active compound III showed a strong herbicidal activity without damaging the culture plants. The test results are shown in the following Table: 1 II III Kg ha Active Compound 1 1 1 Triticum sativum 5 25 Zea mays 5 15 Ppa annua 55 80 80 Sinapis arvensis 80 100 100 Stellaria media 80 100 100 Eohinochloa crus-galli 45 90 85 no damage total damage
Claims (1)
1. insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671670289 DE1670289C3 (en) | 1967-11-28 | 1967-11-28 | s-triazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31140A0 IL31140A0 (en) | 1969-01-29 |
| IL31140A true IL31140A (en) | 1972-10-29 |
Family
ID=5686307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31140A IL31140A (en) | 1967-11-28 | 1968-11-22 | Triazine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT288083B (en) |
| BE (1) | BE724564A (en) |
| BR (1) | BR6804411D0 (en) |
| CH (1) | CH509041A (en) |
| CS (1) | CS182754B2 (en) |
| DE (1) | DE1670289B2 (en) |
| DK (1) | DK128395B (en) |
| ES (1) | ES360803A1 (en) |
| FR (1) | FR1593741A (en) |
| GB (1) | GB1239240A (en) |
| IE (1) | IE32571B1 (en) |
| IL (1) | IL31140A (en) |
| NL (3) | NL6817048A (en) |
| SE (1) | SE351214B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2454910C3 (en) * | 1974-11-20 | 1985-11-21 | Degussa Ag, 6000 Frankfurt | Method and device for the preparation of solutions or suspensions of cyanuric chloride in hydrous organic solvents |
| US4844731A (en) * | 1986-12-27 | 1989-07-04 | Idemitsu Company Co., Ltd. | Triazine derivatives |
-
1967
- 1967-11-28 DE DE1967B0095581 patent/DE1670289B2/en active Granted
-
1968
- 1968-11-21 GB GB1239240D patent/GB1239240A/en not_active Expired
- 1968-11-22 IL IL31140A patent/IL31140A/en unknown
- 1968-11-22 SE SE15964/68A patent/SE351214B/xx unknown
- 1968-11-26 CH CH1762468A patent/CH509041A/en not_active IP Right Cessation
- 1968-11-26 AT AT1147368A patent/AT288083B/en not_active IP Right Cessation
- 1968-11-26 CS CS6800008063A patent/CS182754B2/en unknown
- 1968-11-26 IE IE1441/68A patent/IE32571B1/en unknown
- 1968-11-27 DK DK579368AA patent/DK128395B/en unknown
- 1968-11-28 FR FR1593741D patent/FR1593741A/fr not_active Expired
- 1968-11-28 ES ES360803A patent/ES360803A1/en not_active Expired
- 1968-11-28 BE BE724564D patent/BE724564A/xx unknown
- 1968-11-28 NL NL6817048A patent/NL6817048A/xx unknown
- 1968-11-28 BR BR204411/68A patent/BR6804411D0/en unknown
-
1972
- 1972-07-28 NL NL7210458A patent/NL7210458A/xx unknown
- 1972-07-28 NL NL7210457A patent/NL7210457A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE32571L (en) | 1969-05-28 |
| AT288083B (en) | 1971-02-25 |
| IE32571B1 (en) | 1973-09-19 |
| GB1239240A (en) | 1971-07-14 |
| IL31140A0 (en) | 1969-01-29 |
| NL7210457A (en) | 1972-10-25 |
| BE724564A (en) | 1969-05-28 |
| NL6817048A (en) | 1969-05-30 |
| SE351214B (en) | 1972-11-20 |
| CS182754B2 (en) | 1978-05-31 |
| ES360803A1 (en) | 1970-07-16 |
| DE1670289B2 (en) | 1977-02-10 |
| BR6804411D0 (en) | 1973-02-22 |
| NL7210458A (en) | 1972-10-25 |
| DE1670289A1 (en) | 1972-03-02 |
| CH509041A (en) | 1971-06-30 |
| DK128395B (en) | 1974-04-29 |
| FR1593741A (en) | 1970-06-01 |
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