GB2072507A - Herbicidal composition and process - Google Patents
Herbicidal composition and process Download PDFInfo
- Publication number
- GB2072507A GB2072507A GB8103871A GB8103871A GB2072507A GB 2072507 A GB2072507 A GB 2072507A GB 8103871 A GB8103871 A GB 8103871A GB 8103871 A GB8103871 A GB 8103871A GB 2072507 A GB2072507 A GB 2072507A
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- United Kingdom
- Prior art keywords
- parts
- compound
- formula
- composition
- herbicidal composition
- Prior art date
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- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 18
- 239000002689 soil Substances 0.000 claims abstract description 13
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 42
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- UMIKSKXLXOFXHG-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl] n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=S)OCC1=CC=C(Cl)C=C1 UMIKSKXLXOFXHG-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 241000335053 Beta vulgaris Species 0.000 description 17
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 16
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- 239000004563 wettable powder Substances 0.000 description 15
- 238000002156 mixing Methods 0.000 description 14
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- 229910052708 sodium Inorganic materials 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- -1 Fuller's earth Chemical compound 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
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- 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 8
- 238000011282 treatment Methods 0.000 description 8
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- 238000005507 spraying Methods 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
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- 239000004009 herbicide Substances 0.000 description 6
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- 240000006928 Persicaria lapathifolia Species 0.000 description 5
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- 235000012629 Mentha aquatica Nutrition 0.000 description 4
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- 231100000674 Phytotoxicity Toxicity 0.000 description 4
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- 244000038559 crop plants Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229920005551 calcium lignosulfonate Polymers 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 235000009973 maize Nutrition 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
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- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000013414 Chenopodium album var centrorubrum Nutrition 0.000 description 1
- 240000002754 Chenopodium giganteum Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 229920005550 ammonium lignosulfonate Polymers 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003918 triazines Chemical class 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
Classifications
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Abstract
A herbicidal composition is provided which is characterized by the combination use as active ingredients of a thiocarbamate derivative of formula I: <IMAGE> wherein one of X and Y is a hydrogen and the other is a chlorine and 4- amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one of the formula: <IMAGE> Also provided is a process of inhibiting the growth of unwanted plants by applying the herbicidal composition to the plants or to the soil where the plants are grown.
Description
SPECIFICATION
Herbicidal composition and process
This invention relates to a herbicidal composition and, more particularly, to a herbicidal composition comprising a thiocarbamate derivative and a triazine derivative in combination as
active ingredients, and to herbicidal processes using the composition.
In recent years, many herbicides have been developed and put to practical applications, resulting in the saving of labor in agricultural works. However, since there occurred various
problems on efficacy and safety of the herbicidal chemicals in the practical applications thereof,
the arrival of further improved herbicides has earnestly been desired. Namely, the related art is
strongly requiring highly safe herbicides which have no affection on useful crops, which
effectively act against harmful weeds at a low application rate and which give no environmental
pollution.
The object of this invention is to provide a herbicidal composition and process adaptable to
such requirements.
The compounds of formula I to be used in the composition according to this invention are
known as an effective herbicide for killing a variety of annual gramineous weeds such as
Echinochloa spp., Digitaria spp., Setaria spp. and Poa annua spp. and annual Cyperus spp. and
to be useful for weeding in such crops as rice, maize, soybean and beet plants.
The compound of formula II is also known as a herbicide for killing various annual broad
leaved weeds such as Polygonum spp., Chenopodium album, Amaranthus albus and Stellaria
media by treatment during their growing period with such a high security that it does not
substantially damage certain crop plants, notably beet.
However, each of the compounds of formulae I and II is not always effective as a completely
selective herbicide if used in a small amount or at a low concentration for killing weeds growing
in beet farms. Thus, the compounds of formula I have an excellent herbicidal activity against
gramineous weeds by pre-emergence application without affecting beet crops, but are insuffici
ent in a small amount or at a low concentration to completely kill broad-leaved weeds and
gramineous weeds by post-emergence application. On the other hand, the compound of formula
II exhibits an excellent herbicidal activity against broad-leaved weeds by post-emergence
application with a high selectivity that it does not substantially affect beet crops, but is
ineffective against broad-leaved weeds and gramineous weeds by pre-emergence application.
The latter compound is also insufficient in its herbicidal activity when it rains early after
application thereof or against old-aged broad-leaved weeds.
The combination of the two compounds of formulae I and II according to this invention makes
it possible to kill pre-emergence broad-leaved weeds, post-emergence gramineous weeds and
old-aged broad-leaved weeds, which were impossible by application of each single compound.
Thus, the composition of this invention exhibits a significant herbicidal activity against a wide
variety of unwanted weeds including annual gramineous weeds and broad-leaved weeds over
the whole growing periods by pre- and post-emergence applications in a small amount or at a
low concentration. Further, the composition of this invention is resistant to rain after the
application, thus lasting a stable herbicidal activity. The high stability under various conditions,
the high activity particularly against old-aged broad-leaved weeds and the immediate effect of
the composition according to this invention are presumed to be due to the ease of the
compound of formula II to be absorbed into the body of weeds by the aid of the compound of
formula I.
In fact, this invention is based on the discovery that the combination of the compounds of
formulae I and II not only supplies the deficiencies of the application of each single compound
as above-mentioned, but also provides an unexpectedly high synergistic effect in such a manner
that the composition of this invention can kill both the gramineous weeds and broad-leaved
weeds growing in beet farms simultaneously and exhibit a high herbicidal activity over the
whole growing periods of weeds by pre- and post-emergence applications. It has also been
found that the composition of this invention is effectively applicable not only to the weeding of
beet farms, but also to that of spinach, barley, wheat and maize farms.
In a further aspect, therefore, the invention provides a process of inhibiting the growth of
weeds in crops of beet, spinach, barley, wheat and maize which comprises applying to the crop
area, before or after the crop emerges, a composition comprising a compound of formula I and a
compound of formula II as active ingredients in an amount sufficient to inhibit the growth of the
weeds but insufficient substantially to damage the crop plants. In the pre-emergence application,
the composition may be applied to soils in which seeds of the crop plants have been sown,
preferably by spraying. In the post-emergence application, the composition is usually applied to
stalks and leaves of plants, preferably by spraying.
Examples of the compounds of formula I used in the composition of this invention are as
follows:
Compound A
S-(p-chlorobenzyl)-N, N-diethylthiocarba mate
Compound B S-(o-chlorobenzyl)-N , N-diethylth iocarbamate
The synergistic effect of the herbicidal composition of this invention is particularly significant at certain specific ratios of the compound of formula I and the compound of formula II, but the ratio of the two compounds to be incorporated may vary over a relatively wide range. In general, it is desirable to use 0.05 to 10 parts by weight, more preferably 0.125 to 4 parts by weight, and most preferably 0.25 to 2 parts by weight, of the compound of formula II (hereinafter referred to as Compound C) per part by weight of the compound of formula I.
The herbicidal composition of this invention may be prepared in any form of preparations containing typically 0.5 to 80% by weight of the active ingredients, such as wettable powders or grains, emulsions, powders, grains, granules, flowable suspensions and the like.
In preparing the herbicidal composition of this invention, the active ingredients are mixed with a diluent or carrier. Suitable solid diluents or carriers include, for example, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, siliceous sand, calcium carbonate, dolomite, powdered magnesia, Fuller's earth, ammonium sulfate and urea. Suitable liquid diluents or carriers include, for example, alcohols, dioxane, acetone, cyclohexane, methylnaphthalene, dimethylformamide and acetonitrile.
Surface active agents which may be used as emulsifying, dispersing or suspending agent in the composition of this invention may be of the cationic, anionic or non-ionic type. Suitable agents of the cationic type include, for example, quaternary ammonium compounds such as cetyltrimethyl ammonium bromide. Suitable agents of the anionic type include, for example, soaps, salts of aliphatic mono-esters of sulphuric acid such as sodium lauryl sulfate, and salts of sulfonated aromatic compounds such as dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulfonate and butylnaphthalene sulfonate.Suitable agents of the non-ionic type include, for example, the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkyl phenols such as octylphenol, nonylpyenol and octylcresol, the partial esters derived from long chain fatty acids and hexitol anhydrides such as sorbitol monolaurate and the condensation products of the said partial esters with ethylene oxide such as polyoxyethylene sorbitan monolaurate. Various other additives which are conventionally used in formulating herbicidal compositions such as carboxymethylcellulose and acasia gum may also be used.
The dose of the active ingredients of the composition of this invention depends upon weather condition, soil condition, form of the composition, season of the application, method of the application, kind of crop plants, kind of weeds and growth stage of weeds and it is usually in a range of 0.5 to 30 kg, preferably 2 to 12 kg and especially 5 to 8 kg per hectare in the soil treatment or the foliage treatment. The composition is usually applied in a concentration of 500 to 30,000 ppm, preferably 2,000 to 20,000 ppm and especially 5,000 to 10,000 ppm of the active ingredients. In the case of application of the herbicidal composition spraying from an airplane, the concentration of the active ingredients is usually in a range of 10,000 to 75,000 ppm. For example 0.5 to 1.5 kg of the active ingredients is sprayed at a rate of 20 to 50 liter/ha.
Upon applications, the herbicidal composition of this invention in the form undiluted or diluted with water is applied to soils or stalks and leaves of plants as above-mentioned. It is also possible to add other herbicidal chemical(s) to the herbicidal composition of this invention to substantially enhance the herbicidal activity thereof.
Following is a description by way of example only of methods of carrying the invention into effect.
In the following examples, proporitons of respective ingredients incorporated and kinds of carriers used can be varied as desired. Unless otherwise indicated, all parts, percents, ratios and the like are by weight.
Compound (A) Emulsifiable concentrate:
5-80 Percent, preferably 10-70% and most preferably 15-30%, of the active ingredients, wherein the ratio of the compounds of formulae I and Il is 1 : 0.05-10, is dissolved in 5-90%, preferably 30-60%, of a liquid carrier, to which is added 1-40%, preferably 5-20% of an emulsifying agent.
Compound (B) Wettable powder:
5-80 Percent, preferably 20-50%, of the active ingredients, wherein the ratio of the compounds of formulae land II is 1 : 0.05-10, 1-20% preferably 5-10% of a surface active agent and 5-85%, preferably 40-70% of a solid carrier are crushed and mixed well.
Compound (C) Dust:
0.5-10 Percent, preferably 1-5%, of the active ingredients, wherein the ratio of the compounds of formulae I and Il is 1: 0.05-10, is crushed and mixed well with 90-99.5%, preferably 95-99%, of a solid carrier.
Compound (D) Granules
0.5-40 Percent, preferably 2-10%, of the active ingredients, wherein the ratio of the compounds of formulae I and II is 1: 0.05-10, is crushed and mixed well with 60-99.5%, preferably 90-98%, of a solid carrier and the mixture is kneaded with the addition of water, granulated and dried to yield granules.
Example 1 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 30 parts of Compound
A, 20 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 25 parts of fine powdered clay.
Example 2 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 40 parts of Compound
B, 20 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 1 5 parts of diatomaceous earth.
Example 3 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 30 parts of Compound
A, 10 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 35 parts of fine powdered clay.
Example 4 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 40 parts of Compound
B, 10 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 25 parts of fine powdered clay.
Example 5 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 30 parts of Compound
A, 30 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of polyvinylalcohol, 20 parts of white carbon and 1 5 parts of diatomaceous earth.
Example 6 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 50 parts of Compound
A, 2.5 parts of Compound C, 3 parts of polyoxyethylenealkylarylether, 3 parts of calcium lignosulfonate, 30 parts of white carbon and 11.5 parts of fine powdered clay.
Example 7 Wettable powder
A wettable powder is prepared by homogeneously mixing and grinding 5 parts of Compound
B, 50 parts of Compound C, 2 parts of sodium alkylbenzenesulfonate, 3 parts of calcium lignosulfonate, 10 parts of diatomaceous earth and 30 parts of fine powdered clay.
Example 8 Emulsion
An emulsion is prepared by homogeneously mixing 10 parts of Compound A, 20 parts of
Compound C, 6 parts of polyoxyethylenealkylarylether, 4 parts of sodium alkylarylsulfonate and 60 parts of dimethylformamide.
Example 9 Emulsion
An emulsion is prepared by homogeneously mixing 30 parts of Compound B, 5 parts of
Compound C, 4 parts of sodium alkylarylsulfonate, 6 parts of polyoxyethylenealkylarylether and 55 parts of dimethyl sulfoxide.
Example 10 Granules
A composition in the form of granules is prepared by homogeneously mixing and grinding 5 parts of Compound A, 5 parts of Compound C, 2 parts of polyvinylalcohol, 1 5 parts of diatomaceous earth and 73 parts of clay, kneading the ground mixture with the addition of water, granulating the mixture and drying the resulting granules.
Example 11 Granules
A composition in the form of granules is prepared by dissolving 10 parts of Compound A and 0.5 parts of Compound C in 3 parts of dimethylformamide and spraying 86.5 parts of diatomaceous earth in the form of granules with the resulting solution.
Example 12 Granules
A composition in the form of granules is prepared by homogeneously mixing and grinding 1 part of Compound B, 10 parts of Compound C, 1 part of sodium alkylbenzene sulfonate, 5 parts of white carbon, 50 parts of bentonite and 30 parts of talc, kneading the ground mixture, granulating the mixture and drying the resulting granules.
Example 13 Powder
A powder composition is prepared by homogeneously mixing and grinding 3 parts of
Compound B, 1 part of Compound C, 0.5 parts of white carbon and 95.5 parts of clay.
Example 14 Powder
A powder composition is prepared by homogeneously mixing and grinding 8 parts of compound A, 0.5 parts of Compound C, 15 parts of diatomaceous earth, 50 parts of clay and 26.5 parts of talc.
Example 15 Powder
A powder composition is prepared by homogeneously mixing and grinding 0.5 parts of
Compound B, 5 parts of Compound C, 2 parts of white carbon and 94.5 parts of clay.
The following Examples (tests) were performed to demonstrate the excellent herbicidal activity of the composition of this invention. In each test, it is suggested that the use of each single compound gives insufficient herbicidal activity, but the combined use of those compounds according to this invention exhibits a higher herbicidal activity than the simple sum of the activities of respective compounds over a wide range of weeds.
Example 16
This example illustrates the herbicidal activities on a variety of unwanted weeds and the phytotoxicity to beet of compositions according to this invention by pre-emergence treatment.
Thirty (30) seeds each of beet (Beta vulgaris), barnyard grass (Echinochloa crusgalli), annual bluegrass (Poa annua), smartweed (Polygonum lapathifolium) and goosefoot (Chenopodium album var. centrorubrum Makino) were sown in farm-soil contained in each of 2,000 cm2 polyethylene containers. After covering the seeds with the soil, each of the wettable powders prepared in Examples 1 and 3 in the form diluted with water to give the concentrations of active compounds shown in Table 1 was uniformly sprayed on to the soil at an application rate equivalent to 500 litres per hectare. After the lapse of 25 days from the spraying, the fresh weight of the plants tested was measured, from which the growth inhibition (%) was calculated as follows:
Fresh weight of the plant
grown in the treated plot
Growth inhibition(%) = (1 - I Fresh weight of the plant
grown in the untreated plot
x 100 .. ...111 The results obtained are shown in Table 1. By way of comparison, similar tests were conducted wherein each compound used in the composition above was used separately under the same conditions as above and the results are also shown in Table 1.
Table 1 Herbicidal activity and phytotoxicity to beet
by pre-emergence treatment
Growth inhibition (%)
Application
Compound rate Barnyard Annual
(kg/ha) Beet grass bluegrass Smartweed Goosefoot
A 3 0 89 86 23 19
B 3 0 81 83 25 20
2 0 23 63 100 100
C 1 0 6 20 80 79
A 3 + 0 100 100 100 100
C 2
A 3 + 0 100 100 100 100
C 1
B 3 + 0 100 100 100 100
C 2
B 3 + 0 100 100 100 100
C 1
Example 17
This Example illustrates the herbicidal activities on various unwanted weeds and the phytotoxicity to beet of compositions according to this invention by post-emergence treatment.
In each of 2,000 cm2 polyethylene containers filled with a farm-soil, beet (1.5 to 2 leaved stage), barnyard grass (2 to 2.5 leaved stage), annular bluegrass (1.5 to 2 leaved stage), smartweed (1 to 2 leaved stage) and goosefoot (1.5 to 2 leaved stage) were grown to such degrees as shown in the above brackets, respectively. Each of the wettable powders prepared in
Examples 2 and 4 was diluted with water to give the concentrations of active compounds shown in Table 2 and sprayed onto the stalks and leaves of the growing plants at an application rate of 500 litres per hectare. Twenty days after the spraying, the fresh weight of the plants tested was measured, from which the growth inhibition (%) was calculated according to formula III. The results are as shown in Table 2.
Table 2 Herbicidal activity and phytotoxicity to beet by
treatment on stalks and leaves in growing stage
Growth inhibition (%)
Application
Compound rate Barnyard Annual
(kg/ha) Beet grass bluegrass Smartweed Goosefoot
A 4 0 78 70 13 10
B 4 0 75 70 16 14
2 0 8 14 56 59
C 1 0 4 9 32 40
A 4 + 0 100 100 98 100
C 2
A 4 + 0 96 100 86 93
C 1
B 4 + 0 100 100 100 100
C 2
B 4 + 0 95 100 85 96
C 1
Example 18
This Example illustrates the herbicidal activities on yellow fox tail (Setaria viridis Beauv.) and amaranth (Amaranthus albus) of compositions according to this invention by pre-emergence and post-emergence treatments. Seeds of the test species were placed on the surface of 2,000 cm2 polyethylene containers of soil and covered with 0.5 cm thickness of the soil.Each of the wettable powders prepared in Examples 5 and 4 was diluted with water to give the concentration of active compounds shown in Table 3 and sprayed onto the soil in the preemergence tests and onto the stalks and leaves of the growing plants in the post-emergence tests at an application rate of 500 litres per hectare. Twenty days after the spraying, the fresh weight of the plant tested was measured, from which the growth inhibition (%) was calculated according to formula Ill. The results are shown in Table 3.
Table 3 Herbicidal acitivity by treatement in different growth stages
Application S.v. A.a. S.v.A.a. S.v. A.a. S.v. A.a.
Comp- rate pound (kg/ha) Pre-emergence 0.5 ~ 1L 1 ~ 1.5L 1.5 ~ 2 L 2.5 ~ 3 L 2.5 ~ 3 L 3.5 ~ 4.5 L
A 4 98 53 86 50 42 11 10 0
B 4 100 58 88 52 47 20 13 7 4 4 0 0 92 0 79 0 42
C 1 9 0 0 88 0 51 0 14
A 4 + 100 100 100 100 93 97 60 89
C 4
A 4 + 100 96 100 100 89 92 58 84
C 1
B 4 + 100 100 100 100 96 99 66 92
C 4
B 4 + 100 100 98 100 92 96 60 91
C 1
Untreated - 0 0 0 0 0 0 0 0
S.v.: Setaria viridis Beauv.; A.a.: Amaranthus albus 0.5~1 L: 0.5~1 leaved stage
Claims (9)
1. A herbicidal composition comprising a thiocarbamate derivative of the general formula:
wherein one of X and Y represents a hydrogen atom and the other is a chlorine atom, and 4amino-3-methyl-6-phenyl- 1, 2,4-triazin-5(4H)-one of the formula:
as active ingredients.
2. A herbicidal composition as claimed in Claim 1 wherein the active ingredients are contained at a concentration of 0.5 to 80% by weight.
3. A herbicidal composition as claimed in Claim 1 wherein the ratio of the compound of formula I and the compound of formula II is 1 : 0.05 to 1 10 by weight.
4. A herbicidal composition as claimed in Claim 3 wherein the ratio is 1 : 0.125 to 1 : 4 by weight.
5. A herbicidal composition as claimed in Claim 1 wherein the compound of formula I is S (p-chlorobenzyl)-N, N-diethylthiocarbamate.
6. A herbicidal composition as claimed in Claim 1 wherein the compound of formula I is S (o-chlorobenzyl)-N, N-diethylth iocarba mate.
7. A process of inhibiting the growth of unwanted plants which comprises applying to the plants or to the soil where the plants are grown a herbicidally effective mount of a composition comprising a thiocarbamate derivative of the general formula:
wherein one of X and Y represents a hydrogen atom and the other is a chlorine atom, and 4amino-3-methyl-6-phenyl- 1, 2,4-triazin-5(4H)-one of the formula:
as active ingredients.
8. A process as claimed in Claim 7 wherein the composition is applied at a rate of 0.5 to 30 kg of the active ingredients per hectate.
9. A process as claimed in Claim 8 wherein the application rate is 2 to 12 kg of the active ingredients per hectare.
1 0. A herbicidal composition as claimed in claim 1 and substantially as described in any one of the specific examples hereinbefore set forth.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2059880A JPS56118004A (en) | 1980-02-22 | 1980-02-22 | Herbicidal composition |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2072507A true GB2072507A (en) | 1981-10-07 |
GB2072507B GB2072507B (en) | 1983-06-02 |
Family
ID=12031702
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8103871A Expired GB2072507B (en) | 1980-02-22 | 1981-02-09 | Herbicidal compositon and process |
Country Status (10)
Country | Link |
---|---|
JP (1) | JPS56118004A (en) |
CS (1) | CS219947B2 (en) |
DE (1) | DE3106407A1 (en) |
FR (1) | FR2477837B1 (en) |
GB (1) | GB2072507B (en) |
IT (1) | IT1167832B (en) |
NL (1) | NL8100829A (en) |
PL (1) | PL126706B1 (en) |
RO (1) | RO81509B (en) |
SU (1) | SU1079163A3 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0362633A2 (en) * | 1988-10-05 | 1990-04-11 | Bayer Ag | Selective herbicidal agents containing metamitron in combination with certain triazolinones |
EP4295686A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
EP4295684A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
EP4295685A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
EP4295687A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5521004B1 (en) * | 1968-10-31 | 1980-06-06 | ||
DE2413298A1 (en) * | 1974-03-20 | 1975-09-25 | Bayer Ag | Means for selective weed control in turnips |
DE2528302A1 (en) * | 1975-06-25 | 1977-01-13 | Bayer Ag | Selective herbicide for beet and soya beans - contg. 3-methyl 4 amino 6 phenyl 1,2,4 triazin 5 one and 4 methoxy benzyl diethyl thiolcarbamate |
-
1980
- 1980-02-20 CS CS801239A patent/CS219947B2/en unknown
- 1980-02-22 JP JP2059880A patent/JPS56118004A/en active Pending
-
1981
- 1981-02-09 GB GB8103871A patent/GB2072507B/en not_active Expired
- 1981-02-17 PL PL1981229716A patent/PL126706B1/en unknown
- 1981-02-19 NL NL8100829A patent/NL8100829A/en not_active Application Discontinuation
- 1981-02-20 FR FR8104052A patent/FR2477837B1/en not_active Expired
- 1981-02-20 SU SU813247947A patent/SU1079163A3/en active
- 1981-02-20 IT IT09340/81A patent/IT1167832B/en active
- 1981-02-20 DE DE19813106407 patent/DE3106407A1/en not_active Ceased
- 1981-02-21 RO RO103483A patent/RO81509B/en unknown
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0362633A2 (en) * | 1988-10-05 | 1990-04-11 | Bayer Ag | Selective herbicidal agents containing metamitron in combination with certain triazolinones |
EP0362633A3 (en) * | 1988-10-05 | 1991-08-14 | Bayer Ag | Selective herbicidal agents containing metamitron in combination with certain triazolinones |
EP4295686A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
EP4295684A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
EP4295685A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
EP4295687A1 (en) * | 2022-06-22 | 2023-12-27 | Adama Agan Ltd. | Agrochemical herbicidal composition |
WO2023248223A1 (en) * | 2022-06-22 | 2023-12-28 | Adama Agan Ltd. | Method of application of herbicidal active ingredients in different stages |
Also Published As
Publication number | Publication date |
---|---|
CS219947B2 (en) | 1983-03-25 |
FR2477837B1 (en) | 1985-06-07 |
IT8109340A0 (en) | 1981-02-20 |
PL126706B1 (en) | 1983-08-31 |
GB2072507B (en) | 1983-06-02 |
DE3106407A1 (en) | 1982-02-11 |
RO81509B (en) | 1983-04-30 |
IT1167832B (en) | 1987-05-20 |
RO81509A (en) | 1983-04-29 |
PL229716A1 (en) | 1981-10-16 |
FR2477837A1 (en) | 1981-09-18 |
SU1079163A3 (en) | 1984-03-07 |
NL8100829A (en) | 1981-09-16 |
JPS56118004A (en) | 1981-09-16 |
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