IL44050A - Method and compositions containing halo-acetanilides together with an antidote from the class of halo alkanoylamides for selective control of weeds in corn - Google Patents
Method and compositions containing halo-acetanilides together with an antidote from the class of halo alkanoylamides for selective control of weeds in cornInfo
- Publication number
- IL44050A IL44050A IL44050A IL4405074A IL44050A IL 44050 A IL44050 A IL 44050A IL 44050 A IL44050 A IL 44050A IL 4405074 A IL4405074 A IL 4405074A IL 44050 A IL44050 A IL 44050A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- antidote
- chloroacetanilide
- radical
- maize
- Prior art date
Links
- 239000000729 antidote Substances 0.000 title claims abstract description 56
- 240000008042 Zea mays Species 0.000 title claims abstract description 29
- 235000002017 Zea mays subsp mays Nutrition 0.000 title claims abstract description 28
- 241000196324 Embryophyta Species 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title abstract description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 title description 3
- 235000005822 corn Nutrition 0.000 title description 3
- 125000001475 halogen functional group Chemical group 0.000 title 1
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 39
- 239000004009 herbicide Substances 0.000 claims abstract description 30
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims abstract description 25
- 235000009973 maize Nutrition 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 238000009331 sowing Methods 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 25
- -1 alkylthio radical Chemical class 0.000 claims description 17
- 239000002689 soil Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 8
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- DAVOZYNLPXEIEH-UHFFFAOYSA-N aniline;azane Chemical compound N.NC1=CC=CC=C1 DAVOZYNLPXEIEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 abstract description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229940075522 antidotes Drugs 0.000 description 12
- 235000013339 cereals Nutrition 0.000 description 10
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 244000038559 crop plants Species 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 208000014674 injury Diseases 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000006394 Sorghum bicolor Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YQCMKAVTVONKPD-UHFFFAOYSA-N 1,2-dichloroxanthen-9-one Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3OC2=C1 YQCMKAVTVONKPD-UHFFFAOYSA-N 0.000 description 1
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- DUUXRKLEZRWLBZ-UHFFFAOYSA-N 2-(hydroxyamino)-n-phenylacetamide Chemical compound ONCC(=O)NC1=CC=CC=C1 DUUXRKLEZRWLBZ-UHFFFAOYSA-N 0.000 description 1
- UGIUIFDIFSBIBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-dimethylanilino)acetic acid Chemical compound CC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl UGIUIFDIFSBIBH-UHFFFAOYSA-N 0.000 description 1
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- 102100028637 CLOCK-interacting pacemaker Human genes 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 101000766839 Homo sapiens CLOCK-interacting pacemaker Proteins 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010633 broth Nutrition 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JOVVGMNSPGGXIW-UHFFFAOYSA-N methyl 3-(n-(2-chloroacetyl)-2,6-dimethylanilino)propanoate Chemical compound COC(=O)CCN(C(=O)CCl)C1=C(C)C=CC=C1C JOVVGMNSPGGXIW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UCPWEJNQKVUTLV-UHFFFAOYSA-N propan-2-ylcarbamodithioic acid Chemical class CC(C)NC(S)=S UCPWEJNQKVUTLV-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 208000037974 severe injury Diseases 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (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)
Abstract
1454043 Herbicide/antidote composition CIBA-GEIGY AG 24 Jan 1974 [25 Jan 1973] 03293174 Heading A5E A method of selectively combating weeds at a locus comprises (a) applying to the locus before, during or after sowing maize seed therein; or (b) applying to maize seed itself prior to sowing in the locus either simultaneously, or successively in either order: i) a compound of formula I: wherein: R 1 represents a methyl or methoxy group; and ii) a compound of the formula II: wherein R 2 and R 3 , which may be the same or different, each represent an allyl or C 1 -C 4 alkyl group, or together with the nitrogen atom to which they are bonded represent an unsubstituted or 2-methyl substituted 1, 3-oxazolidine ring, the amount of ii) being sufficient to protect the maize seeds or germinating maize shoots from attack by i). Compositions of i) and ii) also are claimed. Compound i) is N-(2'-methoxyethyl)-2, 6-dimethyl-chloroacetanilide or N-(2'- methoxyethyl) - 2 - methyl - 6 - methoxy - chloroacetanilide; typical compounds ii) are N, N-diallyl-dichloroacetamide; N-allyl-N-ethyl-dichloroacetamide and 2, 2-dimethyl-3-dichloroacetyl-1, 3-oxazolidine. Specification 1396941 is referred to.
[GB1454043A]
Description
It is known that many herbicides in important of cultivated plants have no, or too little, selective action, i.e. in addition to the weeds to be destroyed they also injure the cultivated plants to a greater or lesser degree.
This applies to most classes of herbicide, e.g. triazines, urea derivatives, carbamates, thiolcarbamates , haloacetani-lides etc.
This property has particularly disadvantageous consequences in large scale crops, such as cereals and maize, and despite successful efforts to find herbicides of good selectivity, this problem has still not been completely satisfactorily solved .
On the other hand, substances have been proposed for pretreating seeds, e.g. for providing cereal and maize seeds with protective layers before sowing in order to make them resistant to specific herbicides. Both the protective agent and the herbicide are very largely species -specific with respect to the cultivated plant. Thus in German Offenlegungsschrift 1.952. 910 and in French patent 2.021.611 (Gulf), the use of 1, 8-naphthalic acid derivatives, oxamic acid derivatives (derivatives of the oxylic monoamide H00C-CO H2) and malonic diamide has been proposed for treating cereal and maize seeds in order to protect these against attack by herbicidal N, N-dialkylated thiocarbamic acid-S-alkyl esters. Earlier, proposals had already been made for treating cereal seeds with the most diverse substances, js!-!&h as hydroxyaminoacetanilide , dichloroxanthenones , hydantoins, isopropyldithiocarbamate salts, N-meth 1-dichlorobenzene-sulphonamide etc., in order to protect the seeds against the action of herbicidal carbamates, such as IPC, CIPC (German patent 1.576.076, US patent 3.131.509 (Gulf).
Of more recent date are publications relating to the treatment of the seeds and shoots of corn and sorghum with Ν,Ν-disubs tituted oxamic acid esters, diallyl prop)Tion-amide, diallyl acetamide, naphthalates etc. in order to protect these against attack by N-methoxymethyl- (2 ' , 6 ' -diethyl-chloroacetanilide) , cf. British patent 1.277.557 (Gulf).
This particular seed treatment before sowing entails substantial economic disadvantages, in particular the expenditure in terms of labour and money involved in the special steps carried out in special mixing devices for the large amounts of seeds which are sown in large-scale crops .
Attempts have therefore already been made to find what are known as safening agents or antidotes which can be applied not to the seeds, but either together with, or before or after, the herbicidal application to the crop area to be sown, or which has already been sown (preemergent treatment) , or after the seeds have germinated (post-emergent treatment) , and which have the same protective effect, i!.^/. they cause the non-selective herbicide to act selectively in that the weeds are damaged as much as possible without any more injury to the cultivated plants. Belgian patent 771.928 and German Offenlegungsschrift (Stauffer) describe such an agent for protecting cereals against the herbicidal action of thiolcarbamates and triazines. Besides these herbicides, this agent contains as antidote halogenated alkanesulphonates of the type X-(CH2)n-0-S02-R wherein X represents a halogen atom, R represents alkyl, haloalkyl, halogen, acetoxy (halo) -alkyl, aryl, and n is a whole number from 1 to 5.
Here too a pronounced species -specificity of the herbicides and the antidote on cereals is evident.
Finally, there has recently appeared a publication (German Offenlegungsschrift 2.218.097, Stauffer) in which, besides a straight forward pretreatment of the seeds with an halogenated alkoylamides , there are also described herbi-cidal agents which contain such haloall^oylamides as anti-dotes.
The majority of the antidotes described and tested therein are used specifically with respect to the active components in the application of herbicidal thiolcarbamates and mixtures thereof with other herbicidal active subs tsif!oes . The emphasis is clearly on antagonising undesirable injury to the crop plants by thiolcarbamates . It is true that this publication does also mention among the herbicides to be protected chloroacetanilides as mixture components and individual active substances. However, the individual tests with such active substances refer only to two herbicides of this type, namely N-methoxymethyl-2, 6-diethyl-chloro-acetanilide ("LASSO") without antidote and with an uneconomic surplus of an antidote in sorghum vulgare, and N-isopropyl-chloroacetanilide ("RAMROD") without antidote and with a surplus of antidote in corn. Despite the surplus of antidote, the result in both cases was far from convincing, the decrease in injury of the crop plant with the antidote moderate, and the ultimate injury determined still considerable (20%) . It is known that, in contradis trinction to other and recent, more active chloroacetanilides, no antidote at all is required when applying these two herbicides to maize.
It is propably for this reason that, despite a vast number of tests, this publication contains no further example with chloroacetanilides as herbicides. Evidently, the appli-cant of German Offenlegungsschrift 2.2128.097 has not realise the exceptionally important fact that other more active chloroacetanilides of different constitution can be conspicu- ously improved in their selective activity against weeds," _:η· cereals and maize by small amounts of some of the antidotes proposed by her, and for this reason has proposed these antidotes with proven success only together with thiolcarba-mates as herbicides.
Whereas certain herbicides of the triazine and phenylurea series are already known for the selective control of weeds in cereals and maize and are commercially available, it has not been possible to avail of more recent haloacetani-lides to the desired extent on account of their generally unsatisfactory selectivity in cereal and maize plantations, since they cause severe injury to these crop plants, which means diminished yield, and still no effective antidote against such halo^entahilides has become known.
The chloroacetanilides of differing constitution which are used according to the present invention, some of which have recently become known (German Offenlegungsschrift 2.305.495, 2.328.340 and 2212268) and form the subject matter of pending patent applications, have the formula I R 44050/2 wherein and each independently represents hydrogen/ Λ a lower alkyl, haloalkyl, alkoxy, alkoxyalkyl or alkylthio radical or a halogen atom, and R represents ap alkyl radical with 1 to 4 carbon atoms which is substituted by carboxy, carboxylic ester, carboxylic amide or cyano radicals, or repre sents an alkoxyalkyl radical of the formula -A-O-R^, wherein A is an alkylene radical with 2 to 4 carbon atoms of which 1 or 2 are in the direct chain, and R^ represents a lower alkyl or alkenyl radical or a cycloalkyl or cycloalkylmethyl radical with 3 to 6 ring carbon atoms, and further, the phenyl nucleus can carr one or two substituents of the definition given for R^ and R2 which are in meta-position to the aniline-nitrogen.
Preferably, herbicidal chloroacetanilides are used wherein, in the above formula I, R, represents hydrogen or an alkyl radical with 1 to 4 carbon atoms, R2 represents an alkyl radical with 1 to 4 carbon atoms, R represents an alkyl radical with 1 to 4 carbon atoms which is substituted by carboxylic ester radicals, or an alkoxyalkyl radical of the formula -A-O-R^* wherein A is an alkylene radical with 2 or 3 carbon atoms, of which 1 or 2 are in the direct chain, and R^ represents an alkyl or alkenyl radical with 1 to 4 carbon atoms, and further, the phenyl nucleus can carry in addition one lower alkyl or alkoxy radical which is in meta-position to the aniline-nitrogen.
The surprising discovery has now been made thai", contrary to the presumptions to be inferred from the literature, it is possible to impart firstjrate protection to maize plants from injury by the above mentioned herbicidal chloroacetanilides by treating the soil with a halogenated an alkraylamide of the formula II as antidote.
In this formula, and each independently represents optionally halogenated alkyl, alkenyl and alkinyl radicals, optionally halogenated alkoxyalkyl and alkenyloxy alkyl radicals, cycloalkyl or cyanoalkyl radicals, and R^ and Rr, together with the adjacent nitrogen atom, can also form a 5- or 7 -membered/heterocyclic ring which can contain in addition a further heteroatom and can be substituted by lower alkyl radicals.
The invention therefore provides a method for the selective control of weeds in maize cultures, which consist in treating the seeds or the crop areas intended for the cultivation of maize in which the seeds are to be sown, or which have been sown, or in which the seeds have already - - germinated, simultaneously or successively, in optional sequence and in an appropriate interval of time, on the one hand with a herbicide of the group of the chloro-acetanilides of the formula I, and on the other with an an antidote of the series of the halogenated allioylamides of the above formula II which protects the germinated crop plants and/or the seeds thereof.
In the formula I of the herbicidal chloroacetanili-des, R represents preferably a lower alkoxyalkyl radical, in particular methoxyethyl, ethoxyethyl, 3-methoxy-propyl (2) etc. Preferred herbicidal active substances of the formula I are N- (2 ' -methoxyethyl) -2 , 6-dimethyl-chloroacet-anilide, N- [3* -methoxypropy1- (2 ' ) ] -2-methyl-6-ethyl-chloro-acetanilide and other 2, 6-dialkylchloroacetanilides with alkoxyalkyl radicals which contain at least two optionally branched hydrocarbon chain members in the alkyl moiety bonder to the nitrogen.
In the formula II of the antidotes, and preferably represent allyl radicals and/or lower alkyl radicals or together form a 1, 3-oxazolidine ring, which in 2-position can be substituted in addition with advantage by methyl groups.
Besides carriers, the agent for selective control of weeds in maize according to the invention contains as herbicidally active component at least one chloroacetanilide - - of the formula I as well as an antidote of the formula lf^^ These agents can be applied in any suitable form. Thus they can be manufactured in known manner by intimately mixing and grinding the herbicidal active substances and the antidote with suitable carriers and/or additives optionally accompanied by the addition of dispersants or solvents.
The conventional process forms are either solid, such as dusts, tracking agents, granules, or liquid solutions, or they take the form of active substance concentrates which can be dispersed in water, such as wettable powders, emulsions, or pastes.
The agent according to the invention is incorporated into the soil either before or after the maize has been sown. But naturally it is also possible to apply first the herbicide and then the antidote to the soil. Finally, it would also be possible to pretreat the seeds themselves first with the antidote and then to sow them in the soil, which has either been treated with the herbicide or in which the herbicide will later be incorporated. It is essential that the addition of the antidote does not impair the herbicidal action of the chloroacetanilide on the weeds.
The amount of antidote used varies between about 0.01 and about 15 parts by weight per part by weight of the haloacetanilide . According to circumstances, i.e. depending on the chloroacetanilide and antidote used and the crop plant, the most suitable ratio for attaining the most ideal activity is ascertained.
Experiments have proved, for example, that by treating sown maize fields with 2 kg/ha of a chloroacetanilide alone there occurred total injury after 3 1/2 weeks; but treatment with a mixture of the same amount of this chloroacetanilide and 0.5 kg/ha of an antidote caused no injury at all to the maize, while weeds such as Sorghum hybridum, Echinoclea and Setaria were just as completely destroyed as without the antidote.
A number of herbicidal chloroacetanilides of the formula I, which can be applied together with the antidotes .. of the formula II, are listed hereinbelow: N- (2 ' -methoxyethyl) -2, 6-dimethyl-chloroacetanilide N- (2 ' -allyloxyethyl) -2, 6-dimethyl-chloroacetanilide N- (2 ' -n-propyloxyethyl) -2, 6-dimethyl-chloroacetanilide N- (2 ' -isopropyloxyethyl) -2, 6-dimethyl-chloroacetanilide N- (2 ' -methoxyethyl) -2-methy1-6-ethy1-chloroacetanilide N- (2 ' -methoxyethyl) -2, 6-diethyl-chloroacetanilide N- (2 ' -ethoxyethyl) -2-methyl-6 -ethyl-chloroacetanilide N- (11 -ethoxycarbonyl-ethyl) -2, 6-dimethyl-chloroacetanilide N- (3 ' -methoxy-propyl- (21 ) -2-meth 1-chloroacetanilide N- (3 ' -methoxy-propyl- (2 ') -2, 6-dimethyl-chloroacetanilide N- (3 ' -methoxy-propyl- (2 ' ) -2-methyl-6-ethyl-chloroacetanilide Ί N- (3 ' -methoxy-propyl- (2 ' ) -2, 6-diethyl-chloroacetanilide >' N-(3 ' -methoxy-propyl- (2 ' ) -2-ethyl-chloroacetanilide N-(2' -ethoxyethyl) -2, 6-diethyl-chloroacetanilide N-(2 ' -n-propoxyethyl) -2-methyl-6-ethyl-chloroacetanilide N-(2* -n-propoxyethyl) -2, 6-diethyl-chloroacetanilide N-(2' -isopropylethyl) -2-methyl-6-ethyl-chloroacetanilide N-chloroacetyl-2, 6-dimethylanilino-acetic acid ethyl and methyl ester β- (N-chloroacetyl-2, 6-dimethylanilino) -propionic acid methyl ester a-(N-chloroacetyl-2-methyl-6-ethyl-anilino) -propionic acid ethyl ester N-(3 ' -methoxy-propyl- (21 ) -2, 3-dimethyl-chloroacetanilide N- (21 -ethoxyethyl) -2-methyl-6-chloro-chloroacetanilide N-(2' -me tho yethyl) -2-methyl-6-chloro-chloroacetanilide N-(2 * -methoxyethyl) -2-methyl-6 -methoxy-chloroacetanilide The above cited, and further, chloroacetanilides of this type and the manufacture thereof have been described in German Offenlegungsschriften 2.212.268, 2.305.495, 2.328. 340 and in Swiss patent applications 15044/72, 1757/73 of CIBA-GEIGY AG.
Suitable antidotes of the formula II are those which come under this formula and are described in part in German. Offenlegungsschrift 2.218.097.
It is conceivable that an antidote which is used in higher rates of application in cereals itself exerts a herbicidal action, but in small amounts antagonises the herbicidal action of the chloroacetanilides on maize.
Preferred antidotes of the formula II are CH2=CH-CH2 \ ) N-C0-CHC1, N,N-diallyl-dichloroacetamide, CH2=CH-CH2 20 nT 1,5036 ) yl-dichloroacetamide CH2-CH2 0 / N -C0-CHC1 N-dichloroacetyl-2, 2-dimethyl- 1, 3-oxazolidine m.p." 119-121° CH. ai.
Very useful as antidotes are also the following dichloro-acetamides which carry at the amide-nitrogen the groups tabulated here inbe low: q N-CO-CHC R - The following tests were carried out to determine' the selective herbicidal action of chloroacetanilides the formula I alone and together with antidotes of the formula II : Pre-emergent application N- (2 ' -methoxyethy1) -2, 6-dimethyl-chloroacetanilide (A) the formula CH was used as herbicidal active substance.
This compound was manufactured by reacting 2, 6-dimethyl-aniline with methoxyacetaldehyde dissolved in benzene in the presence of trimethylamine by boiling to give l-(2'-methoxy-ethylidene-amino) -2, 6-dimethylbenzene (b.p. 58°-61°C/0.1 Torr) , converting this product by hydrogenatio in ethanol with palladium-charcoal to N- (2 ' -methoxyethy1) -2,6-xylidine (b.p. 64°-65°C/0.2 Torr) , and reacting this latter as a suspension together with potassium bicarbonate in benzene with chloroacetyl chloride. 3 Ν,Ν-diyllyl-dichloroacetamide (B) and N -dichloroacetyl- 2, 2-dimethyl-l, 3-ox Λzolidine (C) were used as antidote, both substances described in German Offenlegungsschrift 2.218.097 (Examples 1 and 42), as well as -ethyl-N-ally1-d ichlord-acetamide (D) and N-isopropyl-N-allyl-dichloroacetamide (E) . Aqueous stock broths (suspensions) were prepared from wettable powders based on substances A, B, C, D, and E, and these suspensions were applied both singly and as mixtures, in the indicated concentrations and mixture ratios, immediately after the test plants had been sown in seed dishes in a greenhouse, to the surface of the soil in the dishes. The seed dishes were then kept for 24 days at 22° to 23° C and 50% to 70% relative humidity while appropriately watering the dishes and the emergent plants. The results were evaluated after 13 and 24 days according to a scale of rating from 1-9: 9 = plants not injured (as untreated control) 1 = plants completely withered 2 to 8 = intermediate stages of injury As test plants there were used: crop plant: maize ("Orlea") [Zea] weeds: Sorghum hybridum Echinochloa crus galli Setaria italica Digitaria sanguinalis Bromus tectorum The results are tabulated below.
The amounts in kg/ha are in the following relation to other / units of measurement: 2 1 k /ha = 0.1 g/m = 2 mg per litre of soil, 2 the depth of the t:eed dishes is 5 cm, so that 1 m = 50 litres of soil.
Table III Plant Herbicide A Antidote D Antidote E amount in after 24 days after 24 days kg/ha amcunt in kg/ha amount i kg/ha 0 2 1 0,5 0 2 1 0,5 0 9 9 9 9 9 9 9 9 Maize 0,5 8 9 9 9 8 9 9 9 1,0 (Or la) 3 9 9 9 3 9 9 9 2,0 2 9 9 2 9 8 0 9 9 9 9 9 9 9 9 So ghum 0,5 2 2 2 2 2 2 2 1 hybridurn 1,0 2 2 2 2 2 2 2 2 2,0 . 1 1 1 1 1 1 0 9 9 9 9 9 9 9 9 Echinochloa 0,5 1 1 1 1 1 1 1 1 crus galli 1,0 1 1 1 1 1 1 1 1 2,0 1 1 1 1 1 1 0 9 9 9 9 9 9 9 9 Seta ia 0,5 2 1 1 1 2 1 1 1 italica i»o 1 1 1 1 1 1 1 1 2,0 1 I 1 1 1 1 0 9 : 9 9 9 9 9 9 9 Digitaria 0,5 1 1 1 1 1 1 1 1 sanguinalis 1,0 1 1 1 1 1 1 1 1 2,0 1 1 1 1 1 1 0 9 9 9 9 9 9 9 9 Bromus 0,5 2 2 2 2 2 2 2 2 tectorum 1,0 1 2 1 1 1 1 2 1 2,0 1 1 1 1 1 1 The results show clearly that the crop plant maiae, which is virtually completely destroyed after 13 days using a rate of application of 2 kg/ha of herbicide A alone, suffers no more injviry at all even after 24 days using the same amount of herbicide together with only 1/4 the amount (0.5 kg/ha) of the antidote B, C, D or E, whereas all weeds are just as severely injured as without the antidote. It can even be seen that better results are often obtained with the application of smaller amounts of antidote than with larger ones. No surplus of antidote is therefore necessary and the ratio of antidote to herbicide can be 1:4.
It is advisable in practice, especially in regions with low rainfall, not only to apply the agent according to the invention to the surface of the soil, but to work it into the soil before the crop plants are sown, thus preventing only the perhaps more soluble herbicide from penetrating into the soil when rainfall is slight and the antidote which remains on the surface from not being sufficiently active.
In the above tests, a surface treatment of the soil alone was sufficient to prove clearly an optimum effectiveness of the antidote.
Similarly good results were attained with other herbicidal chloroacetanilides of the formula I and with other antidotes of the formula II.
Claims (12)
1. A method for the selective control of weeds in maize, which comprises the use of chloroacetanilides as herb ic ideal active substances, and which consists in treating the seeds or the crop areas intended for sowing, or crop areas for the cultivation of maize which have been sown or in which the seeds have already germinated, simultaneously or successively in optional sequence, on the one hand with a herbicide of the group of the chloroacetanilides of the formula I wherein and R2 each independently represents hydrogen, a lower alkyl, haloalkyl, alkoxy, alkoxyalkyl or alkylthio radical or a halogen atom, and R^ represents an alkyl radical with 1 to 4 carbon atoms which is substituted by carboxy, carboxylic ester, carbcxy amide or cyano radicals, or represents an alkoxyalkyl radical of the formula -A-O-R^ in which A is an alkylene radical with 2 to 4 carbon atoms of which 1 or 2 are in the direct chain and R^ represents a lower alkyl or alkenyl radical or a cycloalkyl or cyclo- alkylmethyl radical with 3 to 6 ring carbon atoms, and the phenyl nucleus can carry in addition 1 or 2 subs tituents of the definition given for and R2 which are in meta- position to the aniline-nitrogen, and on the other hand with an antidote of the series of the alkoylamides of the formula II which protects the seeds or germinated maize shoots and plants- from attack by this herbicide, in which formula II R^ and R^ each independently represents optionally halogenated alkyl, alkenyl and alkinyl radicals, optionally halogenated alkoxyalkyl and alkenyloxyalkyl radicals, cyclo- alkyl or cyanoalkyl radicals, or R^ and R^, together with the adjacent nitrogen atom, can also from a 5- to 7-membered /heterocycle which can contain in addition a further hetero- atom be mono- or polysubs tituted by lower alkyl radicals.
2. A method according to claim 1, which consists in applying the active substance of the formula I and the antidote of the formula II before sowing to the surface of the soil of the crop area to be sown or incorporating them thereinto.
3. A method according to claim 1, which consists in treating the soil intended for sowing with the antidote ; [ of the formula II, then sowing, and after the seeds have been sown and the plants have emerged, applying the herbicide of the formula I.
4. A method according to claim 1, which consists in using as antidote of the formula II a dichloroacetamide of the formula 2^ N-CHC12 (III) R6 wherein represents the allyl radical or a lower alkyl radical.
5. A method according to claim 1, which consists in using as antidote 2, 2-dimethyl-3-dichloroacetyl~l, 3-oxazolidine.
6. A method according to claim 1, which consists in using as herbicide a chloroacetanilide of the formula wherein represents hydrogen, methyl or ethyl, R2 represents methyl or ethyl, A represents an ethylene radical or an ethylene radical which is substituted by methyl, and represents an alkyl radical with 1 to 3 carbon atoms.
7. A method according to claim 6, which consists in using N- (21 -methoxyethyl) -2, 6-dimethyl-chloroacetanilide as herbicidal chloroacetanilide.
8. A method according to claim 7, which consists in using N-allyl-N-ethyldichloroacetamide as antidote for this chloroacetanilide .
9. A selective herbicidal agent for controlling weeds in maize, which, in addition to carriers and/or dispersants, contains as herbiqidally active 1 component at least one chloroacetanilide of the formula I according to claim 1, and, as a protective antidote for maize, an alkoxyamide of the formula II according to claim 1.
10. An agent according to claim 9, which contains as herbicidal component a chloroacetanilide of the formula IV according to claim 6, and, as antidote, a dichloroacetamide of the formula III according to claim 4.
11. An agent according to claim 10, which contains as herbicidal component N-(2' -methoxyethyl) -2, 6-dimethyl-chloroacetanilide, and, as antidote, N,N-diallyl-dichloro-acetamide or N-allyl-N-ethyl-dichloroacetamide .
12. An agent according to claim 9, which contains as herbicidal component N- (2 ' -methoxyethyl) -2, 6-d imethyl-chloro acetanilide, and, as antidote, 2 , 2-dimethyl-3 -d ichloroacetyl 1, 3-oxy/zolidine. For fhtf Applicants
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH108373A CH574207A5 (en) | 1973-01-25 | 1973-01-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44050A0 IL44050A0 (en) | 1974-05-16 |
| IL44050A true IL44050A (en) | 1977-02-28 |
Family
ID=4202057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44050A IL44050A (en) | 1973-01-25 | 1974-01-21 | Method and compositions containing halo-acetanilides together with an antidote from the class of halo alkanoylamides for selective control of weeds in corn |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS49102837A (en) |
| CA (1) | CA1168886A (en) |
| CH (1) | CH574207A5 (en) |
| DE (1) | DE2402983A1 (en) |
| FR (1) | FR2215170B1 (en) |
| GB (1) | GB1454043A (en) |
| IL (1) | IL44050A (en) |
| IT (1) | IT1049212B (en) |
| SU (1) | SU582740A3 (en) |
| ZA (1) | ZA74507B (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053297A (en) * | 1975-04-21 | 1977-10-11 | Velsicol Chemical Corporation | Selective herbicidal compositions |
| IT1079199B (en) * | 1976-10-29 | 1985-05-08 | Montedison Spa | ANTIDOTES, OF THE CLASS OF DICHLOROACETAMIDES PARTICULARLY ACTIVE IN PROTECTING MAIZE FROM TOXIC ACTION EXERCISED BY GLYCINE ESTERS N, N SUBSTITUTED HERBICIDE AND HERBICIDE ASSOCIATION FOR MAIZE CULTURES |
| IT1114195B (en) * | 1977-12-23 | 1986-01-27 | Montedison Spa | TWO DICHLOROACETAMIDE ANTIDUCTS FOR NON-SELECTIVE HERBICIDES PARTICULARLY ACTIVE TO PROTECT THE MAIZE FROM TOXIC ACTION EXERCISED BY GLYCIN ESTERS N, N HERBICIDES REPLACED |
| JPS5762205A (en) * | 1977-07-07 | 1982-04-15 | Stauffer Chemical Co | Herbicidal composition for rice fields |
| LU80912A1 (en) * | 1978-02-06 | 1979-06-07 | Nitrokemia Ipartelepek | WEED KILLERS |
| US4174210A (en) * | 1978-03-31 | 1979-11-13 | Chevron Research Company | Herbicidal and plant-growth regulating N-haloacetylphenylamino carbonyl oximes |
| US4260410A (en) * | 1978-03-31 | 1981-04-07 | Chevron Research Company | Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes |
| DE2828303A1 (en) * | 1978-06-28 | 1980-01-17 | Bayer Ag | USE OF N, N-DIALLYL DICHLORACETAMIDE FOR IMPROVING THE CROP PLANT TOLERABILITY OF HERBICIDE-ACTIVE ACETANILIDES |
| DE2832046A1 (en) * | 1978-07-21 | 1980-01-31 | Basf Ag | HERBICIDES BASED ON ACETANILIDES |
| GR66644B (en) * | 1978-07-27 | 1981-04-03 | Basf Ag | |
| DE2832950A1 (en) * | 1978-07-27 | 1980-02-21 | Basf Ag | HERBICIDAL AGENTS |
| DE2832940A1 (en) * | 1978-07-27 | 1980-02-14 | Basf Ag | HERBICIDAL AGENTS |
| US4261733A (en) * | 1978-11-30 | 1981-04-14 | Monsanto Company | Herbicidal compounds and method of preparation and use |
| US4249935A (en) | 1979-07-12 | 1981-02-10 | Basf Aktiengesellschaft | Herbicidal agents |
| DE2930448A1 (en) * | 1979-07-26 | 1981-02-26 | Bayer Ag | COUNTERPROTECTOR FOR THE PROTECTION OF CULTURAL PLANTS FROM HERBICIDE DAMAGE |
| US4294764A (en) | 1979-12-26 | 1981-10-13 | Ppg Industries, Inc. | N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides |
| US4606759A (en) * | 1980-03-25 | 1986-08-19 | Monsanto Company | Herbicidal 2-haloacetanilides |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| CA1168056A (en) * | 1981-10-20 | 1984-05-29 | Attilio Formigoni | Weed-killer composition containing amides as antidotes for alpha-halo-acetanilides |
| ATE20888T1 (en) * | 1982-05-10 | 1986-08-15 | Ciba Geigy Ag | CYCLOPROPANECARBONIC ACID DERIVATIVES. |
| HU193171B (en) * | 1983-07-21 | 1987-08-28 | Eszakmagyar Vegyimuevek | Herbicide preparations containing antidote of n-/dichlor-acetyl/-n-substituted.glycine-n', n-disubstituted-amide-type, or containing agent and antidote, as well as process for the production of the antidote |
| US4734119A (en) | 1983-11-15 | 1988-03-29 | Ciba-Geigy Corporation | Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides |
| US4618361A (en) * | 1983-12-12 | 1986-10-21 | Ciba-Geigy Corporation | Acylamides and compositions for the protection of cultivated plants against the phytotoxic action of herbicides |
| SU1510711A3 (en) * | 1984-05-28 | 1989-09-23 | Циба-Гейги Аг (Фирма) | Weed-killer |
| US5215570A (en) * | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| LT3943B (en) | 1993-12-23 | 1996-05-27 | Ciba Geigy Ag | Remedy for cultured plants protection, use of sulphamoyl-phenyl-carbamides for cultured plant protection, herbicidal preparation, process for preparing sulphamoyl-phenyl-carbamides |
| CN111807984A (en) * | 2020-07-19 | 2020-10-23 | 江苏云帆化工有限公司 | A New Process for Synthesis of Acechlor |
| CN113979880A (en) * | 2021-11-15 | 2022-01-28 | 上海农帆生物科技有限公司 | A kind of new method for preparing dimethachlor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US4033756A (en) * | 1971-09-17 | 1977-07-05 | Gulf Research & Development Company | Dichloroacetamide treated rice seeds |
-
1973
- 1973-01-25 CH CH108373A patent/CH574207A5/xx not_active IP Right Cessation
-
1974
- 1974-01-18 IT IT19576/74A patent/IT1049212B/en active
- 1974-01-18 CA CA000190455A patent/CA1168886A/en not_active Expired
- 1974-01-21 IL IL44050A patent/IL44050A/en unknown
- 1974-01-22 DE DE2402983A patent/DE2402983A1/en active Pending
- 1974-01-23 FR FR7402197A patent/FR2215170B1/fr not_active Expired
- 1974-01-23 SU SU7401989303A patent/SU582740A3/en active
- 1974-01-24 GB GB329374A patent/GB1454043A/en not_active Expired
- 1974-01-24 ZA ZA740507A patent/ZA74507B/en unknown
- 1974-01-25 JP JP49011351A patent/JPS49102837A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA74507B (en) | 1974-12-24 |
| CH574207A5 (en) | 1976-04-15 |
| FR2215170B1 (en) | 1976-11-19 |
| DE2402983A1 (en) | 1974-08-01 |
| SU582740A3 (en) | 1977-11-30 |
| GB1454043A (en) | 1976-10-27 |
| FR2215170A1 (en) | 1974-08-23 |
| JPS49102837A (en) | 1974-09-28 |
| IL44050A0 (en) | 1974-05-16 |
| CA1168886A (en) | 1984-06-12 |
| IT1049212B (en) | 1981-01-20 |
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