CN112741097A - Herbicidal compositions comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides and their use - Google Patents

Herbicidal compositions comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides and their use Download PDF

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CN112741097A
CN112741097A CN202010953693.1A CN202010953693A CN112741097A CN 112741097 A CN112741097 A CN 112741097A CN 202010953693 A CN202010953693 A CN 202010953693A CN 112741097 A CN112741097 A CN 112741097A
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evaluation
cas number
actual control
inhibitors
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CN112741097B (en
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彭学岗
张景远
赵德
崔琦
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Jiangsu Qingyuan Nongguan Weed Control Co ltd
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Jiangsu Qingyuan Nongguan Weed Control Co ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
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    • A01N43/82Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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    • A01N37/22Biocides, 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 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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    • A01N37/26Biocides, 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 containing the group; Thio analogues thereof
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    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
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    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/501,3-Diazoles; Hydrogenated 1,3-diazoles
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    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/601,4-Diazines; Hydrogenated 1,4-diazines
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/70Diamino—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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract

The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing an N- (1,3, 4-oxadiazole-2-yl) aryl formamide compound and application thereof. The composition comprises an active ingredient A and an active ingredient B with herbicidally effective amounts, wherein the active ingredient A is

Description

Herbicidal compositions comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides and their use
Technical Field
The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing an N- (1,3, 4-oxadiazole-2-yl) aryl formamide compound and application thereof.
Background
Chemical weeding is the most economic and effective means in preventing and removing weeds in farmlands, but the problems of drug resistance and resistance evolution of weeds and the like are easily caused by using a single variety or a single action mode of chemical herbicide continuously at a high dose for a long time. The reasonable compounding or mixing of the herbicide compound has the advantages of expanding the weed spectrum, improving the control effect, delaying the occurrence and development of drug resistance and drug resistance of weeds and the like, and is one of the most effective methods for solving the problems. For example, patent CN103596946A discloses N- (1,3, 4-oxadiazole-2-yl) arylformamide and its use as herbicide, and there is still a need to develop a variety of herbicidal compositions with high safety, broad herbicidal spectrum, synergistic effect and capability of solving the problem of resistant weeds.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides a herbicidal composition comprising an N- (1,3, 4-oxadiazol-2-yl) arylcarboxamide compound and its use. The composition can effectively prevent and kill cyperaceae weeds such as cyperus rotundus, cyperus rotundus and irish rush, gramineae weeds such as barnyard grass, digitaria sanguinalis, barnyard grass and moleplant seed, and broadleaf weeds such as monochoria vaginalis, edible tulip, ludwigia prostrata and rhizoma alismatis in crop fields, and has the characteristics of expanding weed control spectrum, reducing application amount, generating synergistic effect, solving resistant weeds and the like.
A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein,
the active ingredient A is
Figure BDA0002677889110000011
Or a salt thereof;
the active ingredient B is selected from one or more of the following compounds and salts/esters thereof:
(1) HPPD inhibitors: sulcotrione (CAS number: 99105-77-8), mesotrione (CAS number: 104206-82-8), topramezone (CAS number: 210631-68-8), tembotrione (CAS number: 335104-84-2), fluroxypyr (CAS number: 352010-68-5), benzofuranone (CAS number: 473278-76-1), bicyclosulfulone (CAS number: 156963-66-5), diconazole (CAS number: 1622908-18-2), ciclopirox (CAS number: 1855929-45-1), triazophorione (CAS number: 1911613-97-2), benzoxaflutole (CAS number: 1992017-55-6), fenzopyr pyrazole (CAS number: 365400-11-9), pyrazolate (CAS number: 58011-68-0), pyroxadim (CAS number: 82692-44-2), tolpyrate (CAS number: 1101132-67-5), fenquinotrione (CAS number: 1342891-70-6), isoxaflutole (CAS number: 141112-29-0), penflufen (CAS number: 71561-11-0),
Figure BDA0002677889110000021
(2) (ii) a PDS inhibitor: flurtamone (CAS number: 61213-25-0), flurtamone (CAS number: 96525-23-4), diflufenican (CAS number: 83164-33-4), diflufenican (CAS number: 137641-05-5), beflubutamid (CAS number: 113614-08-7), norflurazon (CAS number: 27314-13-2), and fluridone (CAS number: 59756-60-4);
(3) a DOXP inhibitor: clomazone (CAS number: 81777-89-1), bixlozone (CAS number: 81777-95-9);
(4) ALS inhibitors: tribenuron-methyl (CAS number: 101200-48-0), thifensulfuron-methyl (CAS number: 79277-27-3), bensulfuron-methyl (CAS number: 83055-99-6), pyrazosulfuron-ethyl (CAS number: 93697-74-6), thiencarbazone-methyl (CAS number: 317815-83-1), halosulfuron-methyl (CAS number: 100784-20-1), propyrisulfuron (CAS number: 570415-88-2), metazosulfuron-methyl (CAS number: 868680-84-6), rimsulfuron-methyl (CAS number: 122931-48-0), ethoxysulfuron (CAS number: 126801-58-9), pyriminosulfuron-methyl (CAS number: 213464-77-8), flucarbazone-methyl (CAS number: 181274-17-9), mesosulfuron-methyl (CAS number: 208465-21-8), nicosulfuron (CAS number: 111991-09-4), Foramsulfuron (CAS number: 173159-57-4), flumetsulam (CAS number: 98967-40-9), triafamone (CAS number: 874195-61-6), penoxsulam (CAS number: 219714-96-2), cloransulam-methyl (CAS number: 147150-35-4), pyroxsulam (CAS number: 422556-08-9), imazamox (CAS number: 114311-32-9), imazapic (CAS number: 104098-48-8), imazethapyr (CAS number: 81385-77-5), imazapyr (CAS number: 81334-34-1), pyriminobac (CAS number: 147411-69-6), florasulam (CAS number: 145701-23-1), pyribenzoxim (CAS number: 135186-78-6), pyribenzoxim (CAS number: 168088-61-7), Tribenuron-methyl (CAS number: 145026-81-9), imazethapyr (CAS number: 81335-77-5), chlorsulfuron (CAS number: 64902-72-3), cinosulfuron (CAS number: 94593-91-6), cyclosulfamuron (CAS number: 136849-15-5), amidosulfuron (CAS number: 120923-37-7), triasulfuron (CAS number: 82097-50-5), iodosulfuron-methyl sodium salt (CAS number: 144550-36-7), flupyrsulfuron (CAS number: 144740-54-5), flucetosulfuron (CAS number: 412928-75-7), metsulfuron (CAS number: 74223-64-6), triflusulfuron (CAS number: 142469-14-5), sulfosulfuron (CAS number: 141776-32-1), pyrazosulfuron (CAS number: 122548-33-8), Bispyribac-sodium (CAS number: 125401-92-5), and sulfentrazone (CAS number: 139528-85-1);
(5) ACCase inhibitors: clodinafop-propargyl (CAS number: 105512-06-9), pinoxaden (CAS number: 243973-20-8), clethodim (CAS number: 99129-21-2), sethoxydim (CAS number: 74051-80-2), quizalofop-p-ethyl (CAS number: 100646-51-3), tralkoxydim (CAS number: 87820-88-0), fluazifop-p-butyl (CAS number: 69806-50-4), haloxyfop-R (CAS number: 72619-32-0), diclofop-p-methyl (CAS number: 51338-27-3), fenoxaprop-p-ethyl (CAS number: 113158-40-0), cyhalofop-butyl (CAS number: 122008-85-9), clethodim (CAS number: 139001-49-3), metamifop (CAS number: 256412-89-2), oxadiargyl (CAS number: 111479-05-1);
(6) PPO inhibitors: fluroxypyr ether (CAS number: 42874-03-3), fomesafen (CAS number: 72178-02-0), oxadiazon (CAS number: 19666-30-9), oxadiargyl (CAS number: 39807-15-3), sulfentrazone (CAS number: 122836-35-5), pyraclonil (CAS number: 158353-15-2), flumioxazin (CAS number: 103361-09-7), pentoxazone (CAS number: 110956-75-7), tiafenacil (CAS number: 1220411-29-9), saflufenacil (CAS number: 372137-35-4), pyraflufen (CAS number: 129630-19-9), carfentrazone (CAS number: 128621-72-7), butafenacil ester (CAS number: 134605-64-4), fluroxypyr ether ethyl ester (CAS number: 131086-42-5), Fluoroglycofen-ethyl (CAS number: 77501-60-1), fluoroglycofen-ethyl (CAS number: 50594-66-6), triflumimoxazin (CAS number: 1258836-72-4), fluazinam-methyl (CAS number: 117337-19-6), Epyrifenacin (CAS number: 353292-31-6);
(7) PSII inhibitors: atrazine (CAS number: 1912-24-9), prometryn (CAS number: 7287-19-6), simetryn (CAS number: 1014-70-6), terbuthylazine (CAS number: 5915-41-3), terbutryn (CAS number: 886-50-0), ametryn (CAS number: 834-12-8), ipratropium (CAS number: 4147-51-7), fenflurazine (CAS number: 845-52-3), prometryn (CAS number: 1014-69-3), simazine (CAS number: 122-34-9), metribuzin (CAS number: 87-21064-9), ethiprole (CAS number: 64529-56-2), amicarbazone (CAS number: 129909-90-6), metribuzin (CAS number: 41394-05-2), cyanazine (CAS number: 21725-46-2), Chlortoluron (CAS number: 15545-48-9), isoproturon (CAS number: 34123-59-6), diuron (CAS number: 330-54-1), fluometuron (CAS number: 2164-17-2), linuron (CAS number: 330-55-2), buthiuron (CAS number: 34014-18-1), cypermethron (CAS number: 42609-52-9), chlortoluron (CAS number: 1746-81-2), bromuron (CAS number: 3060-89-7), endothel (CAS number: 555-37-3), pyridazinol (CAS number: 40020-01-7), hexazinone (CAS number: 51235-04-2), isoethazine (CAS number: 22936-75-0), prodrazine (CAS number: 1912-26-1), bromacil (CAS number: 314-40-9), Cyclinadine (CAS number: 2164-08-1), terbacil (CAS number: 5902-51-2), methabenzthiazuron (CAS number: 18691-97-9), cyclosulfamuron (CAS number: 1982-49-6), isoxaben (CAS number: 55861-78-4), metoxuron (CAS number: 19937-59-8), cumuron (CAS number: 1982-47-4), trifluoxazine (CAS number: 1258836-72-4), cyclopyromate (CAS number: 499231-24-2), propanil (CAS number: 709-98-8), pyridate (CAS number: 55512-33-9), betalain (CAS number: 13684-56-5), betanin (CAS number: 13684-63-4), bentazone (CAS number: 25057-89-0), bromoxynil octanoate (CAS number: 1689-99-2), Bromoxynil (CAS number: 1689-84-5), ioxynil (CAS number: 1689-83-4);
(8) microtubule assembly inhibitors: trifluralin (CAS number: 1582-09-8), butralin (CAS number: 33629-47-9), pendimethalin (CAS number: 40487-42-1), dithiopyr (CAS number: 97886-45-8), ethambucil (CAS number: 55283-68-6), oryzalin (CAS number: 19044-88-3), flumetsulam (CAS number: 1861-40-1), thiabendazole (CAS number: 117718-60-2), propaquilate (CAS number: 23950-58-5), dichlorvos (CAS number: 1861-32-1) and phorate (CAS number: 36335-67-8);
(9) microtubule combination inhibitors: diacyl-amine (CAS number: 16118-49-3);
(10) VLCFA inhibitors: acetochlor (CAS number: 34256-82-1), butachlor (CAS number: 23184-66-9), pretilachlor (CAS number: 51218-49-6), metolachlor (CAS number: 87392-12-9), mefenacet (CAS number: 73250-68-7), s-metolachlor (CAS number: 178961-20-1), flufenacet (CAS number: 142459-58-3), alachlor (CAS number: 15299-99-7), pyriflufen (CAS number: 447399-55-5), anilofol (CAS number: 64249-01-0), xylenol oxamine (CAS number: 87674-68-8), fentrazamide (CAS number: 158237-07-1), triafamone (CAS number: 212201-70-2), cafenstrole (CAS number: 125306-83-4), Mepiquat chloride (CAS number: 24151-93-7), propisochlor (CAS number: 86763-47-5), alachlor (CAS number: 15972-60-8), diflufenican (CAS number: 67129-08-2), propachlor (CAS number: 1918-16-7), dimethenamid (CAS number: 106700-29-2), Dimesulfazet (CAS number: 1215111-77-5), Fenoxasulfone (CAS number: 639826-16-7);
(11) lipid synthesis (non-acetyl-coa carboxylase) inhibitors: prosulfocarb (CAS number: 52888-80-9), molinate (CAS number: 2212-67-1), prosulfocarb (CAS number: 28249-77-6), benfuresate (CAS number: 68505-69-1), ethofumesate (CAS number: 26225-79-6), triallate (CAS number: 2303-17-5), dichlorfon (CAS number: 1929-77-7), butamolide (CAS number: 2008-41-5), dichlorfon (CAS number: 1134-23-2), pennisetum (CAS number: 61432-55-1) and penflun (CAS number: 85785-20-2);
(12) synthesis of hormones: quinclorac (CAS number: 84087-01-4), fluroxypyr (CAS number: 69377-81-7), fluroxypyr-meptyl (CAS number: 81406-37-3), fluroxypyr (CAS number: 943831-98-9), triclopyr (CAS number: 55335-06-3), clopyralid (CAS number: 1702-17-6), picloram (CAS number: 1918-02-1), aminopyralid (CAS number: 150114-71-9), dicamba (CAS number: 1918-00-9), fluroxypyr (CAS number: 1390661-72-9), 2-methyl-4-chlorophenoxyacetic acid (CAS number: 94-74-6), 2-methyl-4-chloro-phenothiolester (CAS number: 25319-90-8), MCPB (CAS number: 94-81-5), 2-methyl-4-chlorophenoxypropionic acid (CAS number: 93-65-2), sodium 2-methyl-4-chlorophenoxyacetate (CAS number: 3653-48-3),Isooctyl 2-methyl-4-chlorophenoxyacetate (CAS number: 29450-45-1), butyl 2, 4-dichlorophenoxyacetate (CAS number: 94-80-4), isooctyl 2, 4-dichlorophenoxyacetate (CAS number: 25168-26-7), 2, 4-dichlorophenoxyacetic acid (CAS number: 94-75-7), chloroquinolinic acid (CAS number: 90717-03-6), 2-methyl-4-chlorodimethylammonium salt (CAS number: 2039-46-5), 2, 4-dichlorpropionic acid (CAS number: 120-36-5), 2, 4-dichlorbutanoic acid (CAS number: 94-82-6), benazolin (CAS number: 25059-80-7), cyprodinil (CAS number: 858956-08-8), CAS,
Figure BDA0002677889110000041
(13) EPSPS inhibitors: glyphosate (CAS number: 1071-83-6), phosphinothricin (CAS number: 81591-81-3);
(14) a GS inhibitor: glufosinate-ammonium (CAS number: 77182-82-2), bialaphos (CAS number: 35597-43-4), and glufosinate-ammonium (CAS number: 35597-44-5);
(15) PSI inhibitors paraquat (CAS number: 1910-42-5), diquat (CAS number: 6385-62-2);
(16) DHP inhibitors: asulam (CAS number: 3337-71-1);
(17) cellulose synthesis inhibitors: triazinyl flumioxazin (CAS number: 131475-57-5), indexazin (CAS number: 950782-86-2);
(18) other herbicides: oxaziclomefone (CAS number: 153197-14-9), cinmethylin (CAS number: 87818-31-3), indanthrone (CAS number: 133220-30-1), quinclorac (CAS number: 130901-36-8), quintocet (CAS number: 1639426-14-4), prosulfuron (CAS number: 99485-76-4), imazalone (CAS number: 150-68-5), tetflupyrlomet (CAS number: 2053901-33-8).
In the context of the present specification, if the abbreviated forms of the common name of the active compounds are used, all customary derivatives, such as esters and salts, and also isomers, in particular optical isomers, in particular one or more commercially available forms, are included in each case. If the generic name denotes esters or salts, all other customary derivatives, such as other esters and salts, free acids and neutral compounds, and also isomers, in particular optical isomers, in particular one or more commercially available forms, are also included in each case. The chemical name given for a compound means at least one compound covered by the generic name, with compounds generally being preferred. In the case of sulfonamides, such as sulfonylureas, salts also include those formed by exchange of cations with hydrogen atoms in the sulfonamide group. For example, 2-methyl-4-chloro derivatives include, but are not limited to: 2 methyl 4 chloro sodium salt, potassium salt, dimethyl ammonium salt, isopropyl amine salt, etc., and 2 methyl 4 chloromethyl ester, ethyl ester, isooctyl ester, ethyl thioester, etc.; 2,4-D derivatives include, but are not limited to: 2,4-D salts such as sodium salt, potassium salt, dimethylammonium salt, triethanolamine salt, isopropylamine salt, choline and the like, and 2,4-D esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester and the like.
Wherein the A, B weight ratio is 1: 600-200: 1 and 1: 500-100: 1; preferably 1: 300-80: 1 and 1: 200-60: 1; more preferably 1:150 to 50:1 and 1:120 to 30: 1; further preferably 1: 100-20: 1 and 1: 80-15: 1; further preferred are 1:50 to 10:1, 1:30 to 5:1, 1:10 to 4:1 and 1:5 to 1: 1.
In one embodiment, the invention also lists the following specific combinations of component a and component B:
Figure BDA0002677889110000051
Figure BDA0002677889110000061
Figure BDA0002677889110000071
Figure BDA0002677889110000081
Figure BDA0002677889110000091
Figure BDA0002677889110000101
Figure BDA0002677889110000111
Figure BDA0002677889110000121
Figure BDA0002677889110000131
Figure BDA0002677889110000141
Figure BDA0002677889110000151
in another embodiment, each of the components A in the above tables is replaced by a corresponding salt.
In the context of the present invention, the salts of the compounds are preferably in the form of the respective alkali metal, alkaline earth metal or ammonium salts (e.g. dimethylammonium, triethanolammonium, isopropylamine, choline etc.), preferably in the form of the respective alkali metal salts, more preferably in the form of the respective sodium or potassium salts, most preferably in the form of the respective sodium salts.
The mass percentage of A, B in the weeding composition accounts for 1-95% of the total amount, and preferably 10-80%.
The weeding composition also comprises conventional auxiliaries which comprise a carrier and a surfactant.
The term "carrier" herein denotes an organic or inorganic, natural or synthetic substance. They facilitate the application of the active ingredient, the carrier being generally inert and must be agriculturally acceptable, in particular for the treated plant. The carrier may be a solid, such as a clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, or the like; or liquids such as water, alcohols, ketones, petroleum distillates, aromatic or waxy hydrocarbons, chlorinated hydrocarbons, liquefied gases, etc.
Surfactants may include emulsifying, dispersing or wetting agents, which may be ionic or non-ionic. Examples which may be mentioned are salts of polyacrylic acids, lignosulphonates, salts of phenolsulphonic or naphthalenesulphonic acids, polymers of ethylene oxide with aliphatic alcohols or with aliphatic acids or with aliphatic amines and substituted phenols, in particular alkylphenols or arylphenols, sulphosuccinates, taurine derivatives, in particular taurine alkyl esters, and phosphoric esters of alcohols or polyhydroxyethylated phenols, alkylsulfonates, alkylarylsulphonates, alkylsulfates, lauryl ether sulphates, fatty alcohol sulphates, and sulphated hexadec, heptadeca-and octadecanols and sulphated fatty alcohol glycol ethers, and furthermore condensates of naphthalene or naphthalenesulphonic acids with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, polystearylphenyl polyglycol ether, Alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors, and also proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohols, polycarboxylates, polyalkoxylates, polyvinylamines, polyvinylpyrrolidone and copolymers thereof. At least one surfactant is required to be present to facilitate dispersion of the active ingredients in water and to facilitate their proper application to the plant.
The compositions may also contain various other components such as protective colloids, binders, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants, and polymers.
In addition, the composition of the present invention can be mixed with the following active substances, for example, known substances in "the world Wide Specification of New agricultural chemical products", the Chinese agricultural science and technology Press, 2010.9 and the references cited therein. For example, herbicidal active substances mentioned below (remarks: the name of the compound, or the generic name according to the International organization for standardization (ISO), or the chemical name, when appropriate with a code), acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, butachlor, napropamide, R-laevo-napropamide, propanil, mefenacet, diphenoyl-oxamide, diflufenican, flumetsulam, bebutamid, dimethenamid, ethoxybenclamide, flufenacet, methoxyfenacet, metazachlor, isooxachlor, lofluvalinate, dimethenamid, butachlor, propisochlor, mefenamid, flucetochlor, propyzamide, dimethenamid, Terbutamid, dimethenamid, dimethachlor, norfluramine, trifoliamine, chlorantraniliprole, propyzamide, penflufen, napropamide, acetometazachlor, naproxen, fenacet, pyraflufen, metolachlor, clofenamide, butachlor, butamidin, fluazinam, atrazine, simazine, prometryn, cyanazine, simetryn, ametryn, prometryn, ipretryn, fluroxypyr, terbutryn, terbutazine, triazineon, cyhalofop, ganciclovir, prometryn, simazine, triazazine, dimethametrazine, isopentetryn, cycloprozine, terbutryn, sec-butyn, terbutaline, terbutryn, metolachlor, cyhalofop, metolachlor, prometryn, simazine, atrazine, dimethametryn, dimethametin, terbutryn, metolachlor, dimethachlor, dimethozin, atrazine, metolachloraz, metolachlor, metolac, Cyanuric acid, Indaziflam, chlorsulfuron, metsulfuron, bensulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron-methyl, iodosulfuron-methyl sodium, formamidosulfuron, cinosulfuron, triasulfuron, sulfometuron-methyl, nicosulfuron, ethametsulfuron-methyl, amidosulfuron, ethoxysulfuron, cyclosulfamuron-methyl, rimsulfuron, azimsulfuron-methyl, monosulfuron-methyl, primisulfuron-methyl, flusulfuron-methyl, flazasulfuron-methyl, propsulfuron-methyl, prosulfuron-methyl, trifloxysulfuron, triflusulfuron-methyl, metsulfuron-methyl, primisulfuron-methyl, propulsulfuron-methyl, propaferon-methyl, triflusulfuron-methyl, sulfometuron-methyl, pyrisulfuron-methyl, propalis-ethyl, thiuron-methyl, sulfometuron-methyl, sulfometuron-ethyl, sulfometuron-ethyl, sulfofluridone, sulfometuron-ethyl, sulfofluridone, sulfometuron, sulfo, Dicumyl ether, aclonifen, ethoxyfen-ethyl, bifenox, trifluoromethoxyfen, metoxyfen, trifluornitrofen, fluoroglycofen, fluridone, bifenox, dimethofen, fluazifop-butyl, Halosafen, chlortoluron, isoproturon, linuron, diuron, fenpropuron, fluometuron, methabenzthiazuron, benzuron, sulfosulfuron, clofenuron, tebuthiuron, clodinuron, meturon, metoxuron, bromuron, metoxuron, meturon, metoxuron, metoron, Betalain, asulam, tefurazol, avenacalin, anilazine, chlorpropham, dichlofenamate, imazalil, cloropham, Carboxazole, chlorerprocarb, Fenasulam, BCPC, CPPC, Carbasulam, buticarb, thiobencarb, dimethenate, triallate, dichloropetalum, ethiofen, prosulfocarb, cloquintocet, prosulfocarb, dichloropetalum, dichloropetalate, dichloropetal, 2-methyl-4-chloropropionate, 2-methyl-4-chlorobutyric acid, 2,4, 5-nasal discharge propionic acid, 2,4, 5-nasal discharge butyric acid, 2-methyl-4-chloroamine salt, dicamba, woollen boom, varparvax, cypress, triclosan, dichlorfenamic acid, metoclopramide, diclofop-p-ethyl, haloxyfop-methyl, haloxyfop-ethyl, quizalofop-p-ethyl, fenoxaprop-p-ethyl, cyhalofop-butyl, fenoxaprop-p-ethyl, cloroph-ethyl, haloxyfop-ethyl, trifoliate-ethyl, clomazone, paraquat, dixyl, asulam, flutolon, isoproturon, chlorothalofop-ethyl, cyhalofop-p-ethyl, propafen-ethyl, butyfen-ethyl, fluroxypyr, metalaxyl, propafen, propaferin, propafen, glyphosate, anilofos, glufosinate, sulfosate, piperaphos, bialaphos, bensulide, imazapyr, mepyrazine, varroa, amifostine, glufosinate, imazethapyr ammonium salt, imazethapyr, imazamethabenz ester, fluroxypyr, isooctyl fluroxypyr, clopyralid, picloram, triclopyr, dithiopyr, haloxyfen, triclopyr, thiazopyr, flurazinone, aminopyralid, flurazone, diflufenzopyr, butoxyethyl triclopyr, ciodinate, sethoxydim, clethodim, thiacet, sethoxydim, clethodim, carfenflurazone, buthiazole, metribuzin, carfenflurazone, metamitron, fenflurazone, fenpyr, benzone, iodoxynil, bromoxynil, isoflurazone, isofluroxypyr, bensulam, isofluroxypyr, clomazone, ioxynil, dichlobenil, tolfenacet, pyraclonil, Iodobonil, flumetsulam, florasulam, penoxsulam, sulfentrazone, cloransulam, diclosulam, pyroxsulam, fluralin, bispyribac, pyribenzoxim, pyriminobac-methyl, pyrithiobac-methyl, bicyclosulfuron, mesotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, ketoxydipradox, isoxaflutole, fenoxasulfolane, Methiozolin, isopyrafen, pyraflufen, pyraflutole, pyrazotocide, pyraclonil, pyraclofenacetone, flumetsulcotrione, flumetsulam, fenflurazole, fentrazachlor, amicarbazone, fentrazachlor, pyrazachlor, pyraclonil, flumicloram, flumioxazone, fenflurazole, flumicloram, bexapyroxadim, flumicloram, bexadim, flumicloram, benfluroram, flumicl, Phthalidyl ether, Flumezin, pentachlorophenol (sodium), dinol, terbenol, terbutal, pendimethalin, dinitrophenol, chloronitrophenol, dimethomorph, oxadiargyl, oxadiazon, pentoxazone, flumetsulam, mefenoxaprop-p-ethyl, tetrazolyl amine, fluridazin, oxamyl, bromamine, dimethenamid, pyridaben, pyridate, pyrirfalol, quinclorac, bentazone, pyridate, oxaziclorac, benazolin, clomazone, clomeptyl, isoprox, iprodione, propamocarb, cumylfen, indoxacarb, sodium chlorate, dalton, dalapon, trichloroacetic acid, monochloroacetone, hexachloroacetone, tetrafluoropropionic acid, pasture, bromophenol oxime, triazoxide, fentrazol, furamethon, fursulam, ethon, benfurazolin, pyrimethanil, clorac, clodinafop, clorac, cumquat, cumarone, clorac, Thidiazuron, alantin, hydroxybenone, metophenone, saflufenacil, dichlorophosphoric, trichloropropionic acid, Alorac, Diethamquat, Etnipromid, Iphridam, Ipfancarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurflurazone, Tripropindan, Sulglycapin, Sumbelanoline, Campandichlor, Cytopyrimidic acid, thiocyananilide, clethodim, fenclorim, cloquintocet, mequintocet, oxaziclomex, oxabetrinil, pyroxaglim, furazolidone, imazaquin, isoxadifen, dichlormid, halauxin, halauxifen, DOWF, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.
The herbicidal composition further comprises at least one safener selected from the group consisting of:
a) dichlorophenyl pyrazoline-3-carboxylic acid (S1) compounds, preferred compounds are, for example, ethyl 1- (2, 4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S1-1 mefenpyr-diethyl, PM, p. 594-595), and related compounds described, for example, in WO91/07874 and PM (p. 594-595).
b) Dichlorophenyl pyrazole carboxylic acid derivatives, preferred compounds are, for example, ethyl 1- (2, 4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1-2), ethyl 1- (2, 4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1- (2, 4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylate (S1-4), ethyl 1- (2, 4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5), and related compounds as described in EP-A-333131 and EP-A-269806.
c) Triazole carboxylic acids (S1) and preferred compounds are, for example, fenchlorazole (fenchlorazole), i.e. ethyl 1- (2, 4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2, 4-triazole-3-carboxylate (S1-6) and related compounds (see EP-A-174562 and EP-A-346620).
d) 5-benzyl-or 5-phenyl-2-isoxazoline-3-carboxylic acids or 5, 5-diphenyl-2-isoxazoline-3-carboxylic acids, preferred compounds being, for example, ethyl 5- (2, 4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds described in WO91/08202, or ethyl 5, 5-diphenyl-2-isoxazoline-3-carboxylate (S1-9, isoxadifen-ethyl)) or 5 described in the patent application (WO-A-95/07897), n-propyl 5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylate (S1-11).
e) 8-Quinolinyloxyacetic acids (S2) of the class of compounds, preferably 1-methylhexan-1-yl (5-chloro-8-quinolinyloxy) acetate (S2-1, cloquintocet-mexyl), such as PM (p. 195-), (1, 3-dimethylbut-1-yl) (5-chloro-8-quinolinyloxy) acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinyloxy) acetate (S2-3), 1-allyloxypropan-2-yl (5-chloro-8-quinolinyloxy) acetate (S2-4), (ethyl 5-chloro-8-quinolinyloxy) acetate (S2-5), (methyl 5-chloro-8-quinolinyloxy) acetate (S2-6), allyl (5-chloro-8-quinolinyloxy) acetate (S2-7), 2- (2-propyleneiminoyloxy) -1-ethyl (5-chloro-8-quinolinyloxy) acetate (S2-8), 2-oxopropan-1-yl (5-chloro-8-quinolinyloxy) acetate (S2-9), and related compounds described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366.
f) (5-chloro-8-quinolinoxy) propanedioic acid-based compounds, preferred compounds are, for example, diethyl (5-chloro-8-quinolinoxy) malonate, (diallyl (5-chloro-8-quinolinoxy) malonate, (methylethyl (5-chloro-8-quinolinoxy) -malonate and related compounds described in EP-A-0582198.
g) Phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acids, such as 2, 4-dichlorophenoxyacetic acid (and esters) (2,4-D), 4-chloro-2-methylphenoxypropionate (2-methyl-4-chloropropionic acid (mecoprop)), MCPA or 3, 6-dichloro-2-methoxybenzoic acid (and esters) (dicamba).
h) Pyrimidines, such as fenclorim (PM, page 386-387) (═ 4, 6-dichloro-2-phenylpyrimidine),
i) dichloroacetamide-based active compounds, which are frequently used as pre-emergence safeners (soil-working safeners), for example "dichloroallylamine (dichlormid)" (PM, page 270-271) (═ N, N-diallyl-2, 2-dichloroacetamide), "AR-29148" (-3-dichloroacetyl-2, 2, 5-trimethyl-1, 3-oxazolidinone from Stauffer), "benoxacor" (PM, page 74-75) (-4-dichloroacetyl-3, 4-dihydro-3-methyl-2H-1, 4-benzoxazine), "APPG-1292" (-N-allyl-N [ (1, 3-dioxolan-2-yl) -methyl ] dichloroacetamide, from PPG Industries), "ADK-24" (═ N-allyl-N- [ (allylaminocarbonyl) -methyl ] -dichloroacetamide, from Sagro-Chem), "AAD-67" or "AMON 4660" (═ 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane, from nitrkemia or Monsanto), "diclonon" or "ABAS 145138" or "ala b 145138" (═ 3-dichloroacetyl-2, 5, 5-trimethyl-1, 3-diazabicyclo [4.3.0] nonane, from BASF), and "furilazol" or "AMON 13900" (see PM, 482-483) ((RS) -3-dichloroacetyl-5- (2-furyl) -2, 2-dimethyloxazolidinone),
j) dichloroacetone derivative-based active compounds, for example, "AMG 191" (CAS registry No. 96420-72-3) (═ 2-dichloromethyl-2-methyl-1, 3-dioxolane, available from Nitrokemia),
k) oxyimino compounds as active compounds, which are referred to as seed dressing materials, for example "oxabetrinil" (PM, page 689) (═ Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile), which in seed dressing is referred to as safener in order to prevent damage to metolachlor (metallachlor), "fluoroxyfen" (PM, page 467 468) (═ 1- (4-chlorophenyl) -2,2, 2-trifluoro-1-ethanone O- (1, 3-dioxolan-2-ylmethyl) -oxime, which in seed dressing is referred to as safener in order to prevent damage to metolachlor (metallachlor), and "cyanohydrin" or "a-CGA-43089" (PM, page 983) ((Z) -cyanomethoxyimino (phenyl) acetonitrile), which is called safener in seed dressing, to prevent the damage of metolachlor (metolachlor),
l) Thiazolecarboxylic acid ester active compounds, which are known as seed dressing materials, for example "flurazon" (PM, p. 450. 451), (-2-chloro-4-trifluoromethyl-1, 3-thiazole-5-carboxylic acid benzyl ester), which are known as safeners in seed dressing to prevent damage to alachlor (alachlor) and metolachlor,
m) active compounds of the naphthalenedicarboxylic acid derivative class, which are known as seed dressings, for example "naphthalic anhydride" (PM, pp 1009-1010) (═ 1, 8-naphthalic anhydride), which are known as safeners in corn seed dressings to prevent damage to thiocarbamate herbicides,
n) chromanoic acid derivatives such as "ACL 304415" (CAS registry No. 31541-57-8) (═ 2-84-carboxychroman-4-yl) acetic acid available from american cyanamid),
o) active compounds which, in addition to herbicidal action on harmful plants, also have safener action on plants, for example "penetryn (dimerate)" or "AMY-93" (PM, p.302-303) (═ S-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate), "diuron (daimuron)" or "ASK 23" (PM, p.247) (═ 1- (1-methyl-1-phenylethyl) -3-p-tolylurecA), "cumyluron (cumyluron)", "jc-940" ((3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenyl-ethyl) urecA, see JP- cA-60087254), "benzophenone (methoxyphenon)" or "ANK 049" (═ 3,3' -dimethyl-4-methoxy-benzophenone), "CSB" (═ 1-bromo-4- (chloromethylsulfonyl) benzene) (CAS registry No. 54091-06-4, available from Kumiai).
The safener is preferably one or more of isoxadifen (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), mefenpyr (CAS: 135590-91-9), cloquintocet (CAS: 99607-70-2), gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8) and metacamifen (CAS: 129531-12-0).
The compositions of the present invention may be diluted or used directly by the user prior to use. The formulation can be prepared by conventional processing methods, i.e., mixing the active substance with a liquid solvent or solid carrier, and adding one or more surfactants such as dispersants, stabilizers, wetting agents, binders, defoamers, etc.
The specific preparation of the weeding composition is dispersible oil suspending agent, water suspending agent, suspending emulsion, wettable powder, missible oil, water dispersible granule (dry suspending agent), emulsion in water and microemulsion.
In short, the compositions of the present invention may be mixed with solid and liquid additives conventionally used in prior art formulations. The amount of the effective ingredient to be used varies depending on external conditions such as temperature, humidity, the nature of the herbicide to be used, and the like. It may vary widely, for example between 0.001 and 1.0kg/ha, or more of active substance, but preferably between 0.005 and 750g/ha, in particular between 0.005 and 500 g/ha.
The invention also provides an application of the weeding composition in weed control; and to provide a method of controlling unwanted plant growth comprising applying the herbicidal composition to a plant, part of a plant, plant seed, or area where a plant is growing.
In addition, the compositions according to the invention can be applied by spraying to the foliage of the plants to be treated, i.e. to the weeds, in particular to surfaces infested or susceptible to infestation by weeds.
When the herbicidal composition of the present invention is applied, an unexpected synergistic effect is obtained, and the herbicidal activity is more remarkable than the expected sum of the activities using individual herbicides, and the activities of the individual herbicides. The synergistic effect is manifested by reduced application rates, a broader spectrum of weed control, and a faster and longer lasting herbicidal action, which are desirable in the practice of weed control. These new compositions are clearly superior to existing herbicides in terms of the properties described, achieving reduced use and being more environmentally friendly.
The synergistic herbicidal composition of the invention also has the following advantages:
(1) the composition of the invention is environment-friendly and is easy to degrade in the environment.
(2) The weeding composition has low cost and convenient use, and has great economic and social benefits when being popularized and applied.
Detailed Description
The following examples are not intended to limit the invention, but merely to illustrate how the invention may be carried out. These examples show particularly significant effectiveness against certain weeds. Examples are as follows:
A) examples of the embodiments
Dispersible oil-suspension concentrate of A1+ mesotrione (4+ 1: representing 4% A1+ 1% mesotrione, the same applies hereinafter)
A1+ mesotrione + 0.3% citric acid + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ topramezone (3+1)
A1+ topramezone + 5% calcium dodecyl benzene sulfonate + 6% fatty alcohol-polyoxyethylene ether + 8% cardanol-oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ topramezone (3+1)
A1+ carfentrazone-ethyl + 0.2% citric acid + 5% calcium dodecylbenzene sulfonate + 6% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
A1+ benzoxaflutole (4+4) dispersible oil suspending agent
A1+ benzoxaflutole + 5% calcium dodecylbenzenesulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% cardanol-oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
A1+ isoxaflutole (4+4) dispersible oil suspending agent
A1+ isoxaflutole + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ clomazone (4+4)
A1+ clomazone + 4% calcium dodecylbenzene sulfonate + 6% cardanol polyoxyethylene ether + 8% castor oil polyoxyethylene ether + 2.5% organobentonite + 5% 100# solvent oil + methyl oleate
A1+ pyrazosulfuron-ethyl (4+2) dispersible oil suspending agent
A1+ pyrazosulfuron-ethyl, 0.5% urea, 5% calcium dodecylbenzenesulfonate, 8% fatty alcohol-polyoxyethylene ether, 5% castor oil-polyoxyethylene ether, 2.5% organobentonite, 2% fumed silica, 5% 100# solvent oil and methyl oleate
8, A1+ penoxsulam (4+1) dispersible oil suspending agent
A1+ penoxsulam + 5% calcium dodecylbenzene sulfonate + 6% sorbitan monooleate polyoxyethylene ether + 5% castor oil oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspending agent of A1+ imazamox (4+1)
A1+ metoclopramide, 5% calcium dodecyl benzene sulfonate, 8% fatty alcohol-polyoxyethylene ether, 6% cardanol-oxyethylene ether, 2.5% organobentonite, 2% fumed silica, 5% 100# solvent oil and methyl oleate
Dispersible oil suspension agent containing A1 and mebendazole nicotinic acid (4+1)
A1+ mebendazole nicotinic acid + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% cardanol-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ bispyribac-sodium (4+1)
A1+ Bispyribac-sodium, 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 5% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
12, A1+ clethodim (4+2) dispersible oil suspending agent
A1+ clethodim + 5% calcium dodecylbenzene sulfonate + 8% sorbitan monooleate polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 20% 100# solvent oil + methyl oleate
A1+ sethoxydim (4+2) dispersible oil suspension
A1+ sethoxydim, 5% calcium dodecylbenzene sulfonate + 8% polyoxyethylene sorbitan monooleate + 7% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 6% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ quizalofop-p-ethyl (4+2)
A1+ quizalofop-p-ethyl + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 5% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 10% 100# solvent oil + methyl oleate
Dispersible oil suspending agent of A1+ oxyfluorfen (3+1)
A1+ oxyfluorfen + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 20% 100# solvent oil + methyl oleate
16, A1+ oxadiazon (3+1) dispersible oil suspending agent
A1+ oxadiazon + 5% calcium dodecylbenzene sulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 5% 100# solvent oil + methyl oleate
17, A1+ oxadiargyl (3+1) dispersible oil suspending agent
A1, oxadiargyl, 5 percent calcium dodecyl benzene sulfonate, 8 percent fatty alcohol-polyoxyethylene ether, 6 percent castor oil-polyoxyethylene ether, 2.5 percent organic bentonite, 2 percent fumed silica, 15 percent 100# solvent oil and methyl oleate
Aqueous suspension of A1+ atrazine (3+5)
A1+ atrazine + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.25% xanthan gum + 2.5% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
19, A1+ terbuthylazine (3+3) aqueous suspension
A1+ terbuthylazine + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.25% xanthan gum + 2.5% magnesium aluminium silicate + 0.1% defoamer + 3% ethylene glycol + water
Aqueous suspension of A1+ propanil (2+20)
A1+ propanil + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.16% xanthan gum + 1.6% magnesium aluminium silicate + 0.1% defoamer + 3% ethylene glycol + water
21, A1+ bentazone (4+30) aqueous suspension
A1+ bentazone + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.1% xanthan gum + 1.2% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
Dispersible oil suspending agent of A1+ butralin (4+21)
A1+ butralin + 10% decanamide + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 7% castor oil-polyoxyethylene ether + 1% organic bentonite + 1% fumed silica + 15% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ pendimethalin (4+21)
A1+ pendimethalin + 10% capramide + 6% calcium dodecylbenzenesulfonate + 8% fatty alcohol-polyoxyethylene ether + 5% castor oil-oxyethylene ether + 1% organobentonite + 1% fumed silica + 10% 100# solvent oil + methyl oleate
Dispersible oil suspending agent of A1+ butachlor (4+6)
A1+ butachlor + 6% calcium dodecylbenzene sulfonate + 6% fatty alcohol-polyoxyethylene ether + 8% cardanol-polyoxyethylene ether + 3% organobentonite + 3% fumed silica + methyl oleate
25, A1+ pretilachlor (2+4) dispersible oil suspending agent
A1+ pretilachlor + 5% calcium dodecylbenzene sulfonate + 6% fatty alcohol-polyoxyethylene ether + 8% cardanol-oxyethylene ether + 3% organobentonite + 3% fumed silica + methyl oleate
26, A1+ anilofos (4+2) dispersible oil suspension
A1+ anilofos + 5% calcium dodecylbenzenesulfonate + 8% cardanol polyoxyethylene ether + 7% castor oil oxyethylene ether + 3% organobentonite + 3% fumed silica + 12% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A1+ quinclorac (2+10)
A1+ quinclorac + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.0% organobentonite + 2.0% fumed silica + 10% 100# solvent oil + methyl oleate
A1+ fluroxypyr (2+3) dispersible oil suspension
A1+ fluroxypyr, 5% calcium dodecylbenzene sulfonate, 8% phenethylphenol polyoxyethylene ether, 6% castor oil oxyethylene ether, 3% organobentonite, 3% fumed silica, 10% 100# solvent oil and methyl oleate
29, A1+ Chlorofluoropyridine ester (3+1) dispersible oil suspension
A1+ fluroxypyridine ester + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-oxyethylene ether + 2.5% organobentonite + 2% fumed silica + methyl oleate
Dispersible oil suspension agent of A1+ 2-methyl-4-chlorophenoxyacetic acid (3+10)
A1+ 2-methyl-4-chlorophenoxyacetic acid + 6% calcium dodecylbenzene sulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil oxyethylene ether + 2% organobentonite + 2.5% fumed silica + 12% 100# solvent oil + methyl oleate
Aqueous suspension of A1+ glyphosate (4+16)
A1+ glyphosate + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 2.0% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
32, A1+ glufosinate-ammonium (3+15) aqueous suspension
A1+ glufosinate-ammonium + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 2.0% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
Aqueous suspension of A1+ diquat (4+15)
A1+ diquat + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 2.0% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
34, A1+ cinmethylin (4+1) dispersible oil suspending agent
A1+ cycloheptane ether + 5% calcium dodecyl benzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 3% organic bentonite + 2% fumed silica + 12% 100# solvent oil + methyl oleate
35, A2+ mesotrione (4+1) dispersible oil suspension agent
A2+ mesotrione + 0.2% citric acid + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
36, A2+ topramezone (3+1) dispersible oil suspending agent
A2+ topramezone + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 7% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
37, A2+ topramezone (3+1) dispersible oil suspending agent
A2+ carfentrazone-ethyl, 0.2% citric acid, 5% calcium dodecyl benzene sulfonate, 9% fatty alcohol-polyoxyethylene ether, 6% castor oil-polyoxyethylene ether, 2.5% organobentonite, 2% fumed silica, 5% 100# solvent oil and methyl oleate
38, A2+ benzoxaflutole (4+4) dispersible oil suspending agent
A2+ benzoxaflutole + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 9% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
Dispersible oil suspension agent containing A2 and isoxaflutole (4+4)
A2+ isoxaflutole + 0.3% citric acid + 5% calcium dodecylbenzenesulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
A2+ clomazone (4+4) dispersible oil suspension
A2+ clomazone + 6% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 7% castor oil-polyoxyethylene ether + 2.5% organobentonite + 10% 100# solvent oil + methyl oleate
41, A2+ pyrazosulfuron (4+2) dispersible oil suspending agent
A2+ pyrazosulfuron-ethyl, 0.5% urea, 5% calcium dodecylbenzenesulfonate, 7% fatty alcohol-polyoxyethylene ether, 8% castor oil-polyoxyethylene ether, 2.5% organobentonite, 2% fumed silica, 5% 100# solvent oil and methyl oleate
42, A2+ penoxsulam (4+1) dispersible oil suspending agent
A2+ penoxsulam + 5% calcium dodecylbenzene sulfonate + 9% sorbitan monooleate polyoxyethylene ether + 5% castor oil oxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
43, A2+ imazamox (4+1) dispersible oil suspending agent
A2+ metopimox, 5% calcium dodecylbenzene sulfonate, 9% fatty alcohol-polyoxyethylene ether, 5% castor oil-polyoxyethylene ether, 2.5% organobentonite, 2% fumed silica, 5% 100# solvent oil and methyl oleate
Dispersible oil suspension agent containing A2+ mebendazole nicotinic acid (4+1)
A2+ mebendazole nicotinic acid + 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 5% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
45.A2+ bispyribac-sodium (4+1) dispersible oil suspending agent
A2+ Bispyribac-sodium, 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 5% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + methyl oleate
46, A2+ clethodim (4+2) dispersible oil suspending agent
A2+ clethodim + 5% calcium dodecyl benzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 20% 100# solvent oil + methyl oleate
Dispersible oil suspension agent of A2+ sethoxydim (4+2)
A2+ sethoxydim, 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 6% 100# solvent oil + methyl oleate
Dispersible oil suspending agent containing A2 and quizalofop-p-ethyl (4+2)
A2+ quizalofop-p-ethyl + 5% calcium dodecylbenzene sulfonate + 8% fatty alcohol-polyoxyethylene ether + 8% castor oil-polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 6% 100# solvent oil + methyl oleate
49, A2+ oxyfluorfen (3+1) dispersible oil suspending agent
A2+ oxyfluorfen + 5% calcium dodecylbenzene sulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 20% 100# solvent oil + methyl oleate
50, A2+ oxadiazon (3+1) dispersible oil suspension
A2, oxadiazon, 5 percent calcium dodecyl benzene sulfonate, 8 percent fatty alcohol-polyoxyethylene ether, 6 percent castor oil-polyoxyethylene ether, 3 percent organic bentonite, 5 percent 100# solvent oil and methyl oleate
51, A2+ oxadiargyl (3+1) dispersible oil suspending agent
A2, oxadiargyl, 5 percent calcium dodecyl benzene sulfonate, 8 percent fatty alcohol-polyoxyethylene ether, 6 percent castor oil-polyoxyethylene ether, 2.5 percent organic bentonite, 2 percent fumed silica, 15 percent 100# solvent oil and methyl oleate
52, A2+ atrazine (3+5) aqueous suspension
A2+ atrazine + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.22% xanthan gum + 2.2% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
53.A2+ terbuthylazine (3+3) water suspension agent
A2+ terbuthylazine + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.26% xanthan gum + 2.2% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
A2+ propanil (2+20) aqueous suspension
A2+ propanil + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.18% xanthan gum + 1.8% magnesium aluminium silicate + 0.1% defoamer + 3% ethylene glycol + water
55, A2+ bentazone (4+30) aqueous suspension
A2+ bentazone + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.12% xanthan gum + 1.5% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
56.A2+ butralin (4+21) dispersible oil suspending agent
A2+ butralin + 10% decanamide + 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 7% castor oil-polyoxyethylene ether + 1% organic bentonite + 1% fumed silica + 10% 100# solvent oil + methyl oleate
57, A2+ pendimethalin (4+21) dispersible oil suspending agent
A2+ pendimethalin + 10% capramide + 6% calcium dodecylbenzenesulfonate + 9% fatty alcohol-polyoxyethylene ether + 5% castor oil-oxyethylene ether + 1% organobentonite + 1% fumed silica + 10% 100# solvent oil + methyl oleate
58.A2+ butachlor (4+6) dispersible oil suspending agent
A2+ butachlor + 6% calcium dodecylbenzene sulfonate + 9% cardanol polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + methyl oleate
59, A2+ pretilachlor (2+4) dispersible oil suspending agent
A2+ pretilachlor + 5% calcium dodecylbenzene sulfonate + 9% anacardol polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + methyl oleate
Dispersible oil suspension agent of A2+ anilofos (4+2)
A2+ anilofos + 5% calcium dodecylbenzenesulfonate + 9% fatty alcohol-polyoxyethylene ether + 7% castor oil-polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 12% 100# solvent oil + methyl oleate
61.A2+ quinclorac (2+10) dispersible oil suspending agent
A2+ quinclorac + 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 2.5% organobentonite + 10% 100# solvent oil + methyl oleate
62, A2+ fluroxypyr (2+3) dispersible oil suspension
A2+ fluroxypyr, 5% calcium dodecylbenzene sulfonate, 9% phenethylphenol polyoxyethylene ether, 6% castor oil oxyethylene ether, 3% organobentonite, 3% fumed silica, 10% 100# solvent oil and methyl oleate
63.A2+ cyhalopyridine ester (3+1) dispersible oil suspending agent
A2+ fluroxypyridine ester + 5% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-oxyethylene ether + 3% organobentonite + 2% fumed silica + 12% 100# solvent oil + methyl oleate
64, A2+ 2-methyl-4-chlorophenoxyacetic acid (3+10) dispersible oil suspending agent
A2+ 2-methyl-4-chlorophenoxyacetic acid + 6% calcium dodecylbenzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-oxyethylene ether + 2% organobentonite + 1% fumed silica + 12% 100# solvent oil + methyl oleate
65.A2+ glyphosate (4+16) aqueous suspension
A2+ glyphosate + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 1% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
66.A2+ glufosinate (3+15) aqueous suspension
A2+ glufosinate-ammonium + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 1% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
A2+ diquat (4+15) aqueous suspension
A2+ diquat + 5% polycarboxylate + 2% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 1% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + water
68.A2+ cinmethylin (4+1) dispersible oil suspending agent
A2+ cycloheptane ether + 5% calcium dodecyl benzene sulfonate + 9% fatty alcohol-polyoxyethylene ether + 6% castor oil-polyoxyethylene ether + 3% organic bentonite + 2% fumed silica + 10% 100# solvent oil + methyl oleate
The processing equipment of the aqueous suspending agent comprises: mixing kettles, colloid mills, sand mills, shearing machines and the like.
The processing process of the aqueous suspending agent comprises the following steps: putting all materials into a mixing kettle, stirring and mixing, passing through a colloid mill, then entering a sand mill for three-stage sand milling, finally uniformly shearing in a shearing machine, and transferring to a storage tank for filling after the test is qualified.
The processing equipment of the dispersible oil suspending agent comprises the following steps: mixing kettles, colloid mills, sand mills, shearing machines and the like.
The processing process of the dispersible oil suspending agent comprises the following steps: putting all materials into a mixing kettle, stirring and mixing, passing through a colloid mill, then entering a sand mill for three-stage sand milling, finally uniformly shearing in a shearing machine, and transferring to a storage tank for filling after the test is qualified.
B) Test of drug efficacy
Spraying treatment of stems and leaves after seedling:
1) test conditions
1.1) test target
The shaped Cyperus is obtained from Hubei Jingzhou, the shredded Cyperus is obtained from Jiangxi Shang, the monochoria vaginalis is obtained from Hunan Changsha, the rice barnyard grass is obtained from Heilongjiang chang, the edible tulip is obtained from Liaoning Yingkou, the Chinese iris is obtained from Heilongjiang tiger forest, the ludwigia prostrata is obtained from Hunan Changsha, the digitaria is obtained from Anglo-hui, and the oriental waterplantain rhizome is obtained from Liaoning Shenyang. The weeds are cultured by a pot culture method, plastic nutrition bowls with the size of 180 х 140mm are placed in an enamel tray, surface soil (4/5) which is collected from a farmland and is dried and sieved is filled in the enamel tray, the soil humidity is controlled to be 20% at the initial stage, weed seeds with full and uniform seeds are selected, the weed seeds are soaked in warm water with the temperature of 25 ℃ for 6 hours, germination is accelerated in a biochemical incubator (dark) with the temperature of 28 ℃, the weed seeds which are just exposed to the white are uniformly placed on the surface of the soil, and then the enamel tray is covered with 0.5-1cm of soil according to the particle size of the seeds.
1.2) culture conditions
The method is carried out in a controllable sunlight greenhouse, the temperature is 20-30 ℃, the natural illumination is carried out, and the relative humidity is 57-72%. The soil type is loam, the organic matter content is 1.63%, the pH value is 7.1, the alkaline hydrolysis nitrogen is 84.3mg/kg, the quick-acting phosphorus is 38.5mg/kg, and the quick-acting potassium is 82.1 mg/kg.
1.3), instrumentation
3WP-2000 model walking spray tower, Minn Jing agricultural machinery research institute of agricultural department. Ten thousandth electronic balance type GA10 (germany); ZDR2000 intelligent data recorder (hangzhou ze large instruments ltd); SPX type intelligent biochemical incubator (Ningbo Jiangnan Instrument factory).
2) Design of experiments
2.1), reagents
The desired active ingredient a comes from patent CN201911014193.5, and its specific preparation process is as follows:
(1) synthesis of compound a 1:
(1.1) sequentially adding Cpd 1(3g,16mmol,1.0eq) and NaOH (0.72g,18mmol,1.1eq) to 30ml of DMF and then adding Cpd 2(1.28g,16.8mmol,1.05eq) dropwise at 0 ℃ followed by stirring the reaction at 0 ℃ for 1 hour. LCMS detection showed the starting material was essentially reacted to completion with a major new peak. The reaction was poured into 30ml of water, the layers separated, the aqueous phase extracted once with 50ml of ethyl acetate and the organic phase washed three times with saturated brine (50ml), dried, spin dried and isolated by column chromatography to give Cpd 3(3.6g, 91% yield) (colourless oil).
Figure BDA0002677889110000291
(1.2) Cpd 3(3.1g,13mmol,1.0eq) was added to 30ml of THF followed by slow addition of n-BuLi (6.42ml,2.5M,16mmol,1.2eq) at-78 deg.C and stirring of the reaction mixture at-78 deg.C for 0.5 h followed by slow CO addition2After 10min, the reaction solution was slowly warmed to room temperature. LCMS detected product. To the reaction mixture was poured 20ml of water, the layers were separated, the aqueous phase was extracted once with 30ml of ethyl acetate, the aqueous phase was gradually adjusted to pH 4-5 with concentrated hydrochloric acid, filtered and dried to give Cpd 4(3.2g, 87% yield) (white solid).
Figure BDA0002677889110000292
(1.3) to 30ml of pyridine were added sequentially Cpd 4(3.1g,11mmol,1.0eq), Cpd 5(1.66g,16.8mmol,1.5eq) and DMAP (0.13g,1.1mmol,0.1 eq). Then slowly adding SOCl at the temperature of 0 DEG C2(2.0g,16.8mmol,1.5eq), and the reaction was stirred at room temperature for 3 hours. LCMS detected product. After removal of pyridine by concentration, 30ml of water was poured into the reaction mixture, the mixture was separated, the aqueous phase was extracted three times with 30ml of ethyl acetate, the organic phase was washed three times with saturated brine (50ml), dried, spin-dried, and isolated by column chromatography to give compound Cpd 6(2.5g, 63% yield) (white solid).
Figure BDA0002677889110000293
(1.4) to 10ml of dichloromethane were added sequentially Cpd 6(1g,2.8mmol,1.0eq) and m-CPBA (0.54g,3.1mmol,1.1 eq). The reaction was then stirred at room temperature for 1 hour. The LCMS detects the product and the raw materials are basically reacted completely. The reaction was poured into 10ml of water, quenched with sodium bisulfite, separated, the aqueous phase extracted three times with 30ml of dichloromethane, the organic phase washed once with saturated brine (30ml), dried, spun-dried and isolated by column chromatography to give compound a1(0.85g, 82% yield) (off-white solid).
1H NMR(500MHz,DMSO-d6)12.57(s,1H),8.07(dd,J=8.0,7.0Hz,1H),7.82(d,J=8.0Hz,1H),3.57-3.47(m,2H),2.48(s,3H),1.70-1.52(m,2H),1.08-0.93(m,3H).
Figure BDA0002677889110000301
(2) Synthesis of compound a 2:
compound A1(0.5g, 98% purity) was resolved by chiral HPLC (Column: CHIRALPAK IG; Column Size: 3 cm. times.25 cm,5 um; Injection: 3.0 ml; Mobile phase: Hex (0.2% FA): IPA 50: 50; Flow rate: 28 ml/min; Wavelength: UV 254 nm; Temperature:25 ℃; Sample solution: 70mg/ml in EtOH/DCM; Run time 60mins) and concentrated after single crystal diffraction to give A2(R configuration) (0.16g, Rt 10.51min, 100% purity ee, 98%).
Figure BDA0002677889110000302
The active ingredients B required are diconazole, bicyclopyrone, topramezone, triazophone,
Figure BDA0002677889110000303
For the company, others were purchased by the reagent company. The raw medicines are all diluted by using an emulsifier Tween-80 aqueous solution with the content of 0.1 percent and taking acetone as a solvent.
Wherein the content of the first and second substances,
Figure BDA0002677889110000304
from patent CN201911321469.4, the preparation method is as follows:
1) compound a (0.5g, 2.13mmol), compound b (313mg, 2.55mmol), a catalytic amount of TBAB (10mg), DMF (10mL) was placed in a round bottom flask and stirred at room temperature 15 ℃ for 24 h. And (5) detecting a small amount of residual raw materials by liquid quality, and then treating. The reaction was poured into 50mL of water, extracted 2 times with methyl tert-butyl ether (50mL × 2), the organic phase was dried, concentrated, and purified by column chromatography to give compound c (300mg, yield 50%). Compound c is a white solid.
Figure BDA0002677889110000311
(2) Compound c (0.3g, 1.06mmol) and methanol (20mL) were placed in a 100mL single-neck flask, and lithium hydroxide (44.5mg, 1.06mmol) was dissolved in 2mL of water, and slowly added dropwise to the single-neck flask at room temperature, followed by stirring at room temperature for 12 hours. After the reaction of the raw materials is finished, adjusting the pH to 5-6 with 0.5M dilute hydrochloric acid, concentrating, and extracting with water and ethyl acetate. The organic phase was dried and concentrated to give compound d (200mg, yield 70%) as a white solid.
Figure BDA0002677889110000312
(3) Compound d (200mg, 0.74mmol), compound e (75mg, 0.74mmol), DCC (152mg, 0.74mmol), and anhydrous DCM (20mL) were placed in a 100mL round-bottomed flask and reacted at room temperature for 12 hours. After the reaction of the starting materials was completed, the reaction solution was concentrated and separated by column chromatography to give the objective compound (200mg, yield 77%) as a white solid.
Figure BDA0002677889110000313
1H NMR(500MHz,Chloroform-d)δ5.28(q,J=7.0Hz,1H),5.15(s,2H),4.27–4.07(m,3H),3.91–3.73(m,2H),2.04–1.82(m,3H),1.66(d,J=7.0Hz,3H),1.59-1.54(m,1H).
2.2) test treatment
2.2.1), dose setting
When determining the ratio or content of the component A and the component B, the main use purpose of the formula is also considered according to the action characteristics of the two medicaments and the measurement of toxicity and the like. On the basis of preliminary experiments, A, B active ingredients are respectively used singly and mixed in different amounts. Water without drug, containing the same solvent and emulsifier was used as a blank.
2.2.2), test repetition
Each treatment was repeated 4 times, 3 pots each time, and 20 weed seeds were sown per pot for 60 plants each time.
2.3) treatment method
2.3.1), treatment time and number of times
The test was performed 1 time in total. And (3) thinning after 1-1.5 leaf period of weeds, keeping 15 weeds in each pot, keeping 45 weeds in each treatment, and then continuously culturing until 2-3 leaves are treated.
2.3.2), instruments and methods of use
Uniformly placing the cultured test material on a 0.5m area2Spraying stem and leaf by using a 3WP-2000 model walking spray tower on the platform, wherein the liquid spraying amount is 450 kg/hectare, and the spraying pressure is 0.3 MPa. And after all the liquid medicine is sprayed, closing the air valve, opening the spraying tower door after 30 seconds, and taking out the nutrition pot. Then the air valve is opened, 50mL of clean water is sprayed, and the liquid spraying pipe is cleaned.
3) Test method
The potting method is adopted. The weed cultivation is shown in 1.1), and the method is carried out according to 'herbicide in pesticide indoor bioassay test guidelines'. The application method is shown in 2.3.2), and stem and leaf treatment method is adopted. After treatment, the cells were transferred to a greenhouse for conventional culture.
4) Data investigation and statistical analysis
4.1) investigation method
The complete survival weed seedlings are cut off along the soil surface by a blade by adopting an absolute number survey method, and the fresh weight of the weeds is weighed by an analytical balance. For the weeds that have died, the fresh weight is zero.
4.2), investigation time and number of surveys
The investigation was carried out 15 days after the treatment, and was carried out 1 time in total.
4.3), statistical analysis of data
The theoretical fresh weight inhibition rate (E0 ═ X + Y-X Y/100) of each treatment mixed combination is calculated by a Gowing method, and then compared with the actually measured inhibition rate (E), the combined action type of the two mixed combinations on the weeds is evaluated, and when the E-E0 value is more than 10 percent, the effect is synergistic, when the E-E0 value is less than-10 percent, the effect is antagonistic, and when the E-E0 value is between-10 percent and 10 percent, the effect is additive. And the optimal proportion is determined according to factors such as actual control effect, characteristics of the herbicide, balance of the formula and the like. Wherein X is the fresh weight inhibition rate when the dosage of the active component A is P; y is the fresh weight inhibition rate of the active component B when the dosage is Q. The statistical results are shown in tables 1-223 below.
Table 1A 1 evaluation of the actual control and combination of mesotrione mixed to cyperus rotundus
Figure BDA0002677889110000321
Table 2A 1 evaluation of the actual control and combination of topramezone on sedge heterotypii
Figure BDA0002677889110000322
Table 3A 1 evaluation of the actual control and combination of the Cyclofonone mixtures on the action of Cyperus rotundus
Figure BDA0002677889110000331
Table 4A 1 evaluation of the actual control and combination of fluroxypyr and Cyperus rotundus
Figure BDA0002677889110000332
TABLE 5A 1 evaluation of the actual control and combination of Fusulcotrione on Cyperus rotundus
Figure BDA0002677889110000333
TABLE 6A 1 evaluation of the actual control and combination of the Doxodim with the mixture of Cyperus rotundus for Cyperus rotundus
Figure BDA0002677889110000334
Table 7A 1 evaluation of the actual control and combination of topramezone on sedge heterotypii
Figure BDA0002677889110000335
TABLE 8A 1 evaluation of the actual control and Combined Effect of Cyclopyraflutole on Cyperus rotundus
Figure BDA0002677889110000336
TABLE 9A 1 evaluation of the actual control and combination of mesotrione mixed with cyperus rotundus
Figure BDA0002677889110000337
TABLE 10A 1 evaluation of the actual control and combination of isoxaflutole with the blended benzoxaflutole on cyperus rotundus
Figure BDA0002677889110000338
TABLE 11A 1 evaluation of the actual control and combination of isoxaflutole on sedge heterotypic
Figure BDA0002677889110000339
Figure BDA0002677889110000341
TABLE 12A 1 evaluation of the actual control and combination of diflufenican on sedge heterotypii with the compounding of diflufenican
Figure BDA0002677889110000342
TABLE 13A 1 evaluation of the actual control and combination of diflufenican on sedge heterotypii with compounding of diflufenican
Figure BDA0002677889110000343
TABLE 14A 1 evaluation of the actual control and combination of clomazone on cyperus alternifolius
Figure BDA0002677889110000344
TABLE 15A 1 evaluation of actual control and combination of thifensulfuron methyl on monochoria vaginalis
Figure BDA0002677889110000345
TABLE 16A 1 evaluation of the actual control and joint action of the mixed bensulfuron methyl on the monochoria vaginalis
Figure BDA0002677889110000346
TABLE 17A 1 evaluation of the actual control and joint action of pyrazosulfuron-ethyl on monochoria vaginalis
Figure BDA0002677889110000347
TABLE 18A 1 evaluation of the actual control and combination of thidiazuron on monochoria vaginalis
Figure BDA0002677889110000348
Figure BDA0002677889110000351
TABLE 19A 1 evaluation of the actual control and joint action of halosulfuron-methyl on monochoria vaginalis
Figure BDA0002677889110000352
TABLE 20A 1 evaluation of the actual control and combination of rimsulfuron on Ottelia communis
Figure BDA0002677889110000353
TABLE 21A 1 evaluation of the actual control and combination of Flucarbazone-sodium for herba Monochoriae
Figure BDA0002677889110000354
TABLE 22A 1 evaluation of actual control and combination of Mesosulfuron-methyl on monochoria vaginalis
Figure BDA0002677889110000355
TABLE 23A 1 evaluation of actual control and joint action of nicosulfuron on monochoria vaginalis
Figure BDA0002677889110000356
TABLE 24A 1 evaluation of the actual control and combination of the foramsulfuron against monochoria vaginalis
Figure BDA0002677889110000357
TABLE 25A 1 evaluation of the actual control and combined action of flumetsulam on monochoria vaginalis
Figure BDA0002677889110000358
TABLE 26A 1 evaluation of the actual control and combination of the Fluoroketofonamide on monochoria vaginalis
Figure BDA0002677889110000359
TABLE 27A 1 evaluation of the actual control and combined action of penoxsulam on monochoria vaginalis
Figure BDA00026778891100003510
TABLE 28A 1 evaluation of the actual control and combination of the Oncorhynchus vaginalis by the Mixed cloransulam-methyl
Figure BDA00026778891100003511
Figure BDA0002677889110000361
TABLE 29A 1 evaluation of the actual control and combination of pyribenzoxim on monochoria vaginalis
Figure BDA0002677889110000362
TABLE 30A 1 evaluation of actual control and combination of imazamox blended with monochoria herb on monochoria vaginalis
Figure BDA0002677889110000363
TABLE 31A 1 evaluation of the actual control and combination of imazapic with the compounding of imazapic
Figure BDA0002677889110000364
TABLE 32A 1 evaluation of actual control and combination of the sodium iodosulfuron for monochoria vaginalis
Figure BDA0002677889110000365
TABLE 33A 1 evaluation of actual control and combination of Bispyribac-sodium by compounding Bispyribac-sodium
Figure BDA0002677889110000366
TABLE 34A 1 evaluation of the actual control and combination of pinoxaden with the compound pinoxaden
Figure BDA0002677889110000367
TABLE 35A 1 evaluation of the actual control and Combined action of the compounded clethodim on rice Echinochloa crusgalli
Figure BDA0002677889110000368
Figure BDA0002677889110000371
TABLE 36A 1 evaluation of the actual control and Combined action of mixed sethoxydim on Echinochloa crusgalli
Figure BDA0002677889110000372
TABLE 37A 1 evaluation of the actual control and combined action of quizalofop-p-ethyl on rice barnyard grass
Figure BDA0002677889110000373
TABLE 38A 1 evaluation of the actual control and combined action of haloxyfop-R-methyl compounded with haloxyfop-R-methyl on rice barnyard grass
Figure BDA0002677889110000374
TABLE 39A 1 evaluation of the actual control and combination of topramezone on rice barnyard grass
Figure BDA0002677889110000375
TABLE 40A 1 evaluation of the actual control and combination of metamifop for rice barnyard grass
Figure BDA0002677889110000376
TABLE 41A 1 evaluation of the actual control and combination of oxyfluorfen in Cyperus rotundus
Figure BDA0002677889110000377
TABLE 42A 1 evaluation of the actual control and combination of fomesafen to cyperus alternifolius
Figure BDA0002677889110000378
TABLE 43A 1 evaluation of the actual control and combination of oxadiazon on cyperus rotundus
Figure BDA0002677889110000381
TABLE 44A 1 evaluation of the actual control and combination of oxadiargyl on cyperus alternifolius
Figure BDA0002677889110000382
TABLE 45A 1 evaluation of the actual control and combination of sulfentrazone on cyperus rotundus
Figure BDA0002677889110000383
TABLE 46A 1 evaluation of the actual control and combination of pyraclonil with cypermethrin for cyperus rotundus
Figure BDA0002677889110000384
TABLE 47A 1 evaluation of the actual control and combination of flumioxazin on cyperus heterotropoides
Figure BDA0002677889110000385
TABLE 48A 1 evaluation of the actual control and combination of the effect of the clomazone on sedges of allotype
Figure BDA0002677889110000386
TABLE 49 evaluation of the actual control and combination of tiafenacil mixed with nutgrass flatsedge
Figure BDA0002677889110000387
Table 50A 1 evaluation of actual control effect and combined effect of mixed saflufenacil on profiled cyperus rotundus
Figure BDA0002677889110000391
TABLE 51A 1 evaluation of the actual control and Combined action of Mixed carfentrazone-ethyl on sedge heterotypii
Figure BDA0002677889110000392
TABLE 52A 1 evaluation of the actual control and combination of acifluorfen-ethyl to sedge heterotypium
Figure BDA0002677889110000393
TABLE 53 evaluation of actual control and Combined action of acifluorfen mixed with 1 on cyperus alternifolius
Figure BDA0002677889110000394
TABLE 54A 1 evaluation of the actual control and combination of triflumimoxazin against Cyperus rotundus
Figure BDA0002677889110000395
TABLE 55A 1 evaluation of the actual control and combination of atrazine mixed with cyperus alternifolius
Figure BDA0002677889110000396
TABLE 56A 1 evaluation of the actual control and combination of terbuthylazine in the formulation of Cyperus rotundus
Figure BDA0002677889110000397
TABLE 57A 1 evaluation of the actual control and Combined action of the Mixed ametryn against sedges heterotypic
Figure BDA0002677889110000398
TABLE 58A 1 evaluation of the actual control and Combined action of Mixed metribuzin on sedges of allotype
Figure BDA0002677889110000401
TABLE 59A 1 evaluation of the actual control and Combined action of amicarbazone on Cyperus rotundus
Figure BDA0002677889110000402
TABLE 60 evaluation of the actual control and combination of Chloroluron mixed with Cyperus rotundus for cyperus esculentus
Figure BDA0002677889110000403
TABLE 61A 1 evaluation of the actual control and combination of isoproturon compounded on Cyperus rotundus
Figure BDA0002677889110000404
TABLE 62 evaluation of the actual control and Combined action of the herbicidal composition of A1 on cyperus rotundus
Figure BDA0002677889110000405
TABLE 63A 1 evaluation of the actual control and Combined action of trifluoxazine on cyperus alternifolius
Figure BDA0002677889110000406
TABLE 64A 1 evaluation of the actual control and combination of cycloprominate mixtures on cyperus alternifolius
Figure BDA0002677889110000407
TABLE 65A 1 evaluation of the actual control and combination of propanil with cyperus rotundus
Figure BDA0002677889110000408
TABLE 66A 1 evaluation of the actual control and combination of pyridate on cyperus alternifolius
Figure BDA0002677889110000409
TABLE 67A 1 evaluation of the actual control and combination of bentazon blends on sedges of abnormal shape
Figure BDA00026778891100004010
Figure BDA0002677889110000411
TABLE 68A 1 evaluation of the actual control and combination of bromoxynil compounds on cyperus alternifolius
Figure BDA0002677889110000412
TABLE 69 evaluation of the actual control and combination of butralin blended with Cyperus rotundus in Table 69A 1
Figure BDA0002677889110000413
TABLE 70A 1 evaluation of the actual control and combination of pendimethalin blended with cyperus rotundus
Figure BDA0002677889110000414
TABLE 71A 1 evaluation of the actual control and combination of butachlor in mixed form for cyperus alternifolius
Figure BDA0002677889110000415
TABLE 72 evaluation of the actual control and combination of pretilachlor mixed with Cyperus rotundus in Table 72A 1
Figure BDA0002677889110000416
TABLE 73A 1 evaluation of the actual control and combination of S-metolachlor on cyperus alternifolius
Figure BDA0002677889110000417
Figure BDA0002677889110000421
TABLE 74A 1 evaluation of the actual control and combination of flufenacet in combination with Cyperus rotundus
Figure BDA0002677889110000422
TABLE 75A 1 evaluation of the actual control and Combined action of Mixed Sulfoxaden on sedges
Figure BDA0002677889110000423
TABLE 76A 1 evaluation of the actual control and combination of anilofos when blending with anilofos for cyperus rotundus
Figure BDA0002677889110000424
TABLE 77A 1 evaluation of the actual control and combination of prosulfocarb on Chufa
Figure BDA0002677889110000425
TABLE 78A 1 evaluation of the actual control and Combined action of the blended crop of Bisodafop masam
Figure BDA0002677889110000426
TABLE 79 evaluation of the actual control and Combined action of the Mixed Liaodan to the Cyperus rotundus of Table 79A 1
Figure BDA0002677889110000427
TABLE 80A 1 evaluation of the actual control and combination of quinclorac on edible tulip
Figure BDA0002677889110000428
TABLE 81A 1 evaluation of the actual control and Combined Effect of fluroxypyr-compounded on Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000429
Figure BDA0002677889110000431
TABLE 82A 1 evaluation of the actual control and combination of halopyridyl fluoroate on Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000432
TABLE 83A 1 evaluation of the actual control and combination of triclopyr on Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000433
TABLE 84A 1 evaluation of the actual control and combination of clopyralid on edible tulip
Figure BDA0002677889110000434
TABLE 85A 1 evaluation of the actual prevention and combination of Picloram against Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000435
TABLE 86A 1 evaluation of the actual control and combination of aminopyralid on Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000436
TABLE 87A 1 evaluation of the actual efficacy and combined action of dicamba compounded on edible tulip
Figure BDA0002677889110000437
TABLE 88A 1 evaluation of the actual control and combination of fluroxypyr meptyl on Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000438
TABLE 89A 1 evaluation of the actual controlling effect and combined action of 2-methyl-4-chlorophenoxyacetic acid compounded on edible tulip
Figure BDA0002677889110000439
Figure BDA0002677889110000441
TABLE 90A 1 evaluation of the actual control and combination of aminocyclopyrachlor in Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000442
TABLE 91A 1 evaluation of actual control and Combined action of Glyphosate mixture on Ottelia communis
Figure BDA0002677889110000443
TABLE 92A 1 evaluation of actual control and Combined action of the mixed glufosinate-ammonium on monochoria vaginalis
Figure BDA0002677889110000444
TABLE 93A 1 evaluation of actual control and Combined action of the Mixed glufosinate-ammonium on monochoria vaginalis
Figure BDA0002677889110000445
TABLE 94 evaluation of actual control and joint action of diquat mixed with diquat on monochoria vaginalis
Figure BDA0002677889110000446
TABLE 95A 1 evaluation of the actual control and combined action of triazineone flumioxazin on monochoria vaginalis
Figure BDA0002677889110000447
TABLE 96A 1 evaluation of the actual control and combination of the hybrid indoxazine-flumetsulam on monochoria vaginalis
Figure BDA0002677889110000451
TABLE 97A 1 evaluation of the actual control and combination of oxaziclomefone on monochoria vaginalis
Figure BDA0002677889110000452
TABLE 98A 1 evaluation of the actual control and combination of the Rohdea japonica with the mixed cinmethylin
Figure BDA0002677889110000453
TABLE 99A 2 evaluation of the actual control and combination of mesotrione mixed to Fluoritum
Figure BDA0002677889110000454
TABLE 100A 2 evaluation of the actual control and combined action of topramezone on Fluoritum
Figure BDA0002677889110000455
TABLE 101A 2 evaluation of the actual prevention and combination of Fluoritum by blending with Ring Sulfonone
Figure BDA0002677889110000456
TABLE 102A 2 evaluation of the actual control and combined action of Fluoritone on Fluoritum
Figure BDA0002677889110000461
TABLE 103A 2 evaluation of the actual control and combination of Fusulone on Fluoritum
Figure BDA0002677889110000462
TABLE 104A 2 evaluation of the actual control and combination of Fluoritone on Fluoritum by blending with benzobicylon
Figure BDA0002677889110000463
TABLE 105A 2 evaluation of the actual control and combined action of mixedly diazolone on Fluoritum
Figure BDA0002677889110000464
TABLE 106A 2 evaluation of the actual control and combined action of Fluoritone on Fluoritum by blending Cyclopyraflutole
Figure BDA0002677889110000465
TABLE 107A 2 evaluation of the actual control and combination of Fluoritum with mixed triazasulam
Figure BDA0002677889110000466
Table 108A 2 evaluation of actual control effect and combined effect of blended benzoxaflutole on firefly iris
Figure BDA0002677889110000467
TABLE 109A 2 evaluation of the actual control and combination of isoxaflutole on Fluoritum
Figure BDA0002677889110000471
TABLE 110A 2 evaluation of the actual control and joint action of Fluoritan on Fluoritan
Figure BDA0002677889110000472
TABLE 111A 2 evaluation of the actual control and combination of Fluorum by compounding Fluopyram
Figure BDA0002677889110000473
TABLE 112A 2 evaluation of the actual control and combination of Dioscorea Opposita Linne by mixing with clomazone
Figure BDA0002677889110000474
TABLE 113A 2 evaluation of actual control and combination of thifensulfuron methyl
Figure BDA0002677889110000475
TABLE 114A 2 evaluation of actual control and combination of bensulfuron methyl for ludwigia prostrata
Figure BDA0002677889110000476
TABLE 115A 2 evaluation of actual control and combination of pyrazosulfuron-ethyl for ludwigia prostrata
Figure BDA0002677889110000477
Figure BDA0002677889110000481
TABLE 116A 2 evaluation of actual control and combination of thifensulfuron methyl on ludwigia prostrata
Figure BDA0002677889110000482
TABLE 117A 2 evaluation of actual control and combination of halosulfuron-methyl on ludwigia prostrata
Figure BDA0002677889110000483
TABLE 118A 2 evaluation of actual control and combination of rimsulfuron with ludwigia prostrata
Figure BDA0002677889110000484
TABLE 119A 2 evaluation of actual control effect and combined action of Flucarbazone-sodium on ludwigia prostrata
Figure BDA0002677889110000485
TABLE 120A 2 evaluation of actual prevention and combination of Disulfuron methyl for cloves and Polygonum hydropiper
Figure BDA0002677889110000486
TABLE 121A 2 evaluation of actual control effect and joint action of nicosulfuron on ludwigia prostrata
Figure BDA0002677889110000487
TABLE 122A 2 evaluation of actual control and combination of coumarone for ludwigia prostrata
Figure BDA0002677889110000488
TABLE 123A 2 evaluation of the actual control and combined action of flumetsulam on ludwigia prostrata
Figure BDA0002677889110000489
TABLE 124A 2 evaluation of actual control and combination of Symphytum officinale by compounding triafamone
Figure BDA00026778891100004810
Figure BDA0002677889110000491
TABLE 125A 2 evaluation of actual control and combined action of penoxsulam on ludwigia prostrata
Figure BDA0002677889110000492
TABLE 126A 2 evaluation of actual prevention and combination of cloransulam-methyl for ludwigia prostrata
Figure BDA0002677889110000493
TABLE 127A 2 evaluation of the actual control and combination of Liquidambaris syringae with Pyrithiobac sodium
Figure BDA0002677889110000494
TABLE 128A 2 evaluation of actual prevention and combination of imazamox blended with ludwigia prostrata
Figure BDA0002677889110000495
TABLE 129A 2 evaluation of actual control and combination of Dioscorea bulbifera with Memidazolinin
Figure BDA0002677889110000496
TABLE 130A 2 evaluation of actual control and combination of Lonicera caryophyllata with iodosulfuron-methyl sodium
Figure BDA0002677889110000497
Figure BDA0002677889110000501
TABLE 131A 2 evaluation of actual prevention and combination of Bispyribac-sodium for Diospyros hydropiper
Figure BDA0002677889110000502
TABLE 132A 2 evaluation of the actual control and Combined Effect of pinoxaden blended with Datang
Figure BDA0002677889110000503
TABLE 133A 2 evaluation of the actual control and Combined Effect of the Compound clethodim on crabgrass
Figure BDA0002677889110000504
TABLE 134A 2 evaluation of the actual control and Combined Effect of Mixed sethoxydim on crab and Tang
Figure BDA0002677889110000505
TABLE 135A 2 evaluation of the actual control and Combined action of quizalofop-p-ethyl on large crabgrass
Figure BDA0002677889110000506
Figure BDA0002677889110000511
TABLE 136A 2 evaluation of the actual control and joint action of haloxyfop-R-methyl on large crabgrass
Figure BDA0002677889110000512
TABLE 137A 2 evaluation of the actual control and combination of cycloxydim on large crabgrass
Figure BDA0002677889110000513
TABLE 138 evaluation of actual prevention and combination of metamifop mixed with 2 for crab
Figure BDA0002677889110000514
TABLE 139A 2 evaluation of the actual control and joint action of Fluoritan on Fluoritan
Figure BDA0002677889110000515
TABLE 140A 2 evaluation of the actual control and combination of Fluoritan to Fluoritan
Figure BDA0002677889110000516
TABLE 141A 2 evaluation of the actual control and combination of the effect of compounding oxadiazon on firefly iris
Figure BDA0002677889110000517
TABLE 142A 2 evaluation of the actual control and combination of oxadiargyl on Fluoritum
Figure BDA0002677889110000518
Figure BDA0002677889110000521
TABLE 143A 2 evaluation of the actual control and combined action of mixed sulfentrazone on Fluoritum
Figure BDA0002677889110000522
TABLE 144A 2 evaluation of the actual control and combination of pyraclonil with respect to Fluoritum
Figure BDA0002677889110000523
TABLE 145A 2 evaluation of the actual control and combination of flumioxazin on Fluoritum
Figure BDA0002677889110000524
TABLE 146A 2 evaluation of the actual control and combination of Fluoritum by blending pentoxazone
Figure BDA0002677889110000525
TABLE 147A 2 evaluation of the actual control and combination of the Fluoritum by blending tiafenacil
Figure BDA0002677889110000526
TABLE 148A 2 evaluation of the actual control and joint action of saflufenacil on Fluorita was
Figure BDA0002677889110000527
TABLE 149A 2 evaluation of the actual control and combined action of Mixed Toxolone on Fluorita
Figure BDA0002677889110000528
TABLE 150A 2 evaluation of actual prevention and combination of Fluoritum with Fluoritum
Figure BDA0002677889110000529
Figure BDA0002677889110000531
TABLE 151A 2 evaluation of the actual control and combination of Fluoritum with mixed acifluorfen
Figure BDA0002677889110000532
Evaluation of actual control and combined action of triflumimoxazin mixed with table 152A 2 on firefly iris
Figure BDA0002677889110000533
TABLE 153A 2 evaluation of the actual prevention and combination of the Oxydazine mixture on Iris lactuca
Figure BDA0002677889110000534
TABLE 154A 2 evaluation of actual control and joint action of Fluoritum by blending terbuthylazine
Figure BDA0002677889110000535
TABLE 155A 2 evaluation of the actual control and combination of ametryn against Flutter
Figure BDA0002677889110000536
TABLE 156A 2 evaluation of the actual control and combined action of metribuzin on Fluoritum
Figure BDA0002677889110000537
TABLE 157A 2 evaluation of the actual control and combination of amicarbazone on Fluoritum
Figure BDA0002677889110000538
TABLE 158A 2 evaluation of the actual control and combination of Luceruron on Fluoritum
Figure BDA0002677889110000539
Figure BDA0002677889110000541
TABLE 159A 2 evaluation of the actual control and combination of isoproturon on Flutter
Figure BDA0002677889110000542
TABLE 160A 2 evaluation of actual control and joint action of herbicide mixture on Fluorita pallida
Figure BDA0002677889110000543
TABLE 161A 2 evaluation of the actual control and combination of trifluoxazine on Fluoritum
Figure BDA0002677889110000544
TABLE 162A 2 evaluation of the actual control and combination of action of cyclopyromate on Fluoritum
Figure BDA0002677889110000545
Table 163A 2 evaluation of actual control and combination of Diphenna with propanil
Figure BDA0002677889110000546
TABLE 164A 2 evaluation of the actual control and combination of pyridate on Fluoritan
Figure BDA0002677889110000547
TABLE 165A 2 evaluation of the actual control and joint action of bentazon on Fluoritum
Figure BDA0002677889110000548
TABLE 166A 2 evaluation of the actual control and combination of bromoxynil compounds on Fluoritum
Figure BDA0002677889110000549
Figure BDA0002677889110000551
TABLE 167A 2 evaluation of the actual control and joint action of butralin mixed on Fluoritum
Figure BDA0002677889110000552
TABLE 168A 2 evaluation of the actual control and joint action of pendimethalin mixed on Fluoritum
Figure BDA0002677889110000553
TABLE 169A 2 evaluation of the actual control and combined action of butachlor mixed with Fluoritan on Fluorita
Figure BDA0002677889110000554
TABLE 170A 2 evaluation of the actual control and combination of pretilachlor on Fluoritum
Figure BDA0002677889110000555
TABLE 171A 2 evaluation of the actual control and combination of S.ophrax by the mixed s.metolachlor
Figure BDA0002677889110000556
TABLE 172A 2 evaluation of the actual control and combined action of flufenacet mixed with Fluticacet on Fluoritum
Figure BDA0002677889110000557
TABLE 173A 2 evaluation of the actual control and combination of Sulfuron pyraflufen-ethyl on Fluoritum
Figure BDA0002677889110000561
TABLE 174A 2 evaluation of the actual control and combination of Shabarbus-grass phosphorus on Fluorita
Figure BDA0002677889110000562
TABLE 175A 2 evaluation of the actual control and combination of the blended prosulfocarb on Flutter
Figure BDA0002677889110000563
TABLE 176A 2 evaluation of the actual control and combination of the Eben-Dip-Fluoritum
Figure BDA0002677889110000564
TABLE 177A 2 evaluation of the actual control and joint action of mixed pellet on Fluorita (L.) Linnaeus
Figure BDA0002677889110000565
TABLE 178A 2 evaluation of the actual prevention and combination of Quinclorac on Alisma orientale
Figure BDA0002677889110000566
TABLE 179A 2 evaluation of actual control and Combined Effect of fluroxypyr on Alisma orientale compounded
Figure BDA0002677889110000567
TABLE 180A 2 evaluation of actual prevention and combination of Fluoropicolide against Alismatis rhizoma
Figure BDA0002677889110000571
TABLE 181A 2 evaluation of the actual prevention and combination of triclopyr on Alismatis rhizoma
Figure BDA0002677889110000572
TABLE 182A 2 evaluation of the actual prevention and combination of clopyralid to Alisma orientale
Figure BDA0002677889110000573
TABLE 183A 2 evaluation of actual prevention and combination of Aminopyric acid to Alismatis rhizoma
Figure BDA0002677889110000574
TABLE 184A 2 evaluation of actual prevention and combination of Lophathernalin for Alismatis rhizoma
Figure BDA0002677889110000575
TABLE 185A 2 evaluation of the actual prevention and combination of Dicamba compounded with Alisma orientale
Figure BDA0002677889110000576
TABLE 186A 2 evaluation of actual control and combination of CfCPDO to Alismatis rhizoma
Figure BDA0002677889110000577
TABLE 187A 2 evaluation of actual prevention and combination of Alismatis rhizoma with 2-methyl-4-chlorophenoxyacetic acid
Figure BDA0002677889110000578
Figure BDA0002677889110000581
TABLE 188A 2 evaluation of the actual prevention and combination of Cytosporanic acid on Alisma orientale
Figure BDA0002677889110000582
TABLE 189A 2 evaluation of actual control and combination of Glyphosate blends on ludwigia prostrata
Figure BDA0002677889110000583
TABLE 190A 2 evaluation of actual control and combination of glufosinate-ammonium for ludwigia prostrata
Figure BDA0002677889110000584
Evaluation of actual prevention effect and combined effect of table 191A 2 mixed with glufosinate-ammonium on ludwigia prostrata
Figure BDA0002677889110000585
TABLE 192A 2 evaluation of actual control and combination of Dimox to ludwigia prostrata
Figure BDA0002677889110000586
TABLE 193A 2 evaluation of the actual control and combination of triazineammoniol on ludwigia prostrata
Figure BDA0002677889110000587
TABLE 194 evaluation of the actual control and combination of indoxazin-flutolanil to ludwigia prostrata by compounding 194A 2
Figure BDA0002677889110000588
Figure BDA0002677889110000591
Evaluation of actual control effect and combined effect of mixed oxaziclomefone in table 195A 2 on ludwigia prostrata
Figure BDA0002677889110000592
TABLE 196A 2 evaluation of actual control and Combined action of Polygala crotalarioides on Ludwigia prostrata
Figure BDA0002677889110000593
TABLE 197A 1 evaluation of the actual control and Combined Effect of sodium salt compounded with Triazolesulfonylvanine on Cyperus rotundus
Figure BDA0002677889110000594
TABLE 198A 1 evaluation of the actual control and combination of halopyridyl chlorofluoride with sodium salt to Pseudobulbus Cremastrae seu pleiones
Figure BDA0002677889110000595
TABLE 199A 2 evaluation of the actual control and combination of propanil with Fluoritum
Figure BDA0002677889110000596
TABLE 200A 2 evaluation of the actual control and combination of Shabarnyard grass phosphorus mixed with potassium salt on Fluoritum
Figure BDA0002677889110000597
Figure BDA0002677889110000601
TABLE 201 evaluation of actual prevention and combination of potassium salt 2 with 2-methyl-4-chlorophenoxyacetic acid to Alismatis rhizoma
Figure BDA0002677889110000602
TABLE 202A 2 evaluation of actual control and combination of Fenquinotrione on Alismatis rhizoma
Figure BDA0002677889110000603
TABLE 203A 2 evaluation of the actual prevention and combination of beflubutamid to Alisma orientale
Figure BDA0002677889110000604
TABLE 204A 2 evaluation of the actual prevention and combination of Fluazinone to Alismatis rhizoma
Figure BDA0002677889110000605
TABLE 205A 2 evaluation of actual control and combination of fluorescent lights with Bixlozone
Figure BDA0002677889110000606
TABLE 206A 2 evaluation of the actual control effect and combined action of mixed oxazine pyrazosulfuron-ethyl on Fluiseed
Figure BDA0002677889110000607
Figure BDA0002677889110000611
TABLE 207A 2 evaluation of the actual control and combination of fenoxaprop-p-ethyl on large crabgrass
Figure BDA0002677889110000612
Table 208A 2 evaluation of actual control and combined action of cyhalofop-butyl on crab grass
Figure BDA0002677889110000613
TABLE 209 evaluation of actual prevention and combination of prometryn-A2 for Alismatis rhizoma
Figure BDA0002677889110000614
TABLE 210A 2 evaluation of actual prevention and combination of Xicaojing with Alisma orientale
Figure BDA0002677889110000615
TABLE 211A 2 evaluation of actual control and combination of bromoxynil octanoate on ludwigia prostrata
Figure BDA0002677889110000616
TABLE 212 evaluation of actual prevention and combination of Flufotiapyr-methyl and Alismatis rhizoma with A2 mixture
Figure BDA0002677889110000617
TABLE 213A 2 evaluation of the actual control and combination of the Benthiazamide on Fluoritum
Figure BDA0002677889110000621
TABLE 214A 2 evaluation of the actual control and combination of Fluoritan with tetrazolyl oxamide
Figure BDA0002677889110000622
TABLE 215A 2 evaluation of the actual control and combination of fluroxypyr-meptyl ester as a blended ingredient for syringy knotweed
Figure BDA0002677889110000623
TABLE 216 evaluation of actual prevention and combination of Alisma orientale by compounding 2, 4-Dichlorophenoxyacetic acid with A2
Figure BDA0002677889110000624
TABLE 217A 2 evaluation of the actual control and combination of asulam to large crabgrass
Figure BDA0002677889110000625
TABLE 218A 2 evaluation of the actual control and Combined Effect of Tetflupyrolomet on crab
Figure BDA0002677889110000626
TABLE 219 evaluation of actual prevention and combination of Fenoxasulfolane with Alismatis rhizoma by compounding with Feroxasulfolane in A2
Figure BDA0002677889110000627
Figure BDA0002677889110000631
TABLE 220A 2 compounding
Figure BDA0002677889110000632
Evaluation of actual prevention effect and combined action of alisma orientale
Figure BDA0002677889110000633
TABLE 221A 2 compounding
Figure BDA0002677889110000634
Evaluation of actual prevention effect and combined action of alisma orientale
Figure BDA0002677889110000635
TABLE 222A 2 evaluation of the actual prevention and combination of Dimesufazet for Fluoritum
Figure BDA0002677889110000636
Table 223A 2 evaluation of actual control effect and combined effect of Ephrifenacil mixed with fluorescent strip
Figure BDA0002677889110000637
C) Demonstration of field
The herbicidal compositions prepared in examples 1 to 68 were used for field weed effect tests. An exemplary promotional trial was conducted in 2017 at the Jiangxi Poyang test point. The weeds in the field are mainly: barnyard grass, moleplant seed, monochoria vaginalis, cyperus rotundus, ludwigia prostrata and the like.
The test method comprises the following steps: treating stem and leaf until the weeds are in the 2-3 leaf stage, manually spraying with a sprayer, and adding water with the amount of 30 kg/667 m2The stem and leaf are sprayed evenly. The specific test agents and dosages are detailed in table 224, with a cell area of 20 square meters, repeated 3 times per treatment. The control effect 20 days after application is shown in Table 224.
Figure BDA0002677889110000641
Table 224 shows exemplary field effects of the formulated compositions
Figure BDA0002677889110000642
Figure BDA0002677889110000651
Through a large number of tests and explorations, the invention unexpectedly discovers that the composition is used for preventing and killing weeds such as heterotype nutgrass flatsedge, cyperus rotundus, monochoria vaginalis, barnyard grass, edible tulip, japanese iris, ludwigia prostrata, digitaria sanguinea, rhizoma alismatis, barnyard grass, moleplant seed and the like, has a surprising and unexpected synergistic effect, is more obvious in performance under low dosage, can reduce the dosage and the pollution to the environment, is reasonably compounded, reduces the agricultural cost, is efficient to ALS and ACCase inhibitor resistant weeds, and has a good application prospect. Meanwhile, the herbicide composition shows good selectivity and excellent synergistic effect in wheat fields, corn fields, paddy fields, peanuts, sugarcane, sorghum, millet, potatoes, rape, soybeans, cotton, vegetables, bluegrass, tall fescue, zoysia japonica and other plants through tests, and can be developed into herbicide mixtures with wide market value.

Claims (10)

1.A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides, which comprises a herbicidally effective amount of an active ingredient A and an active ingredient B, wherein,
the active ingredient A is
Figure FDA0002677889100000011
Or a salt thereof;
the active ingredient B is selected from one or more of the following compounds and salts/esters thereof:
(1) HPPD inhibitors: sulcotrione, mesotrione, topramezone, tembotrione, fluroxypyr, mesotrione, bicyclosulfuron, topramezone, trazodone, triazophone, topramezone, pyrazote, pyraflutole, tolpyralate, fenquinotrione, isoxaflutole, pyraclonil, fenflurazone, topramezone,
Figure FDA0002677889100000012
(2) (ii) a PDS inhibitor: flurtamone, diflufenican, beflubutamid, fluroxypyr and fluridone;
(3) a DOXP inhibitor: clomazone, bixlazone;
(4) ALS inhibitors: tribenuron-methyl, thifensulfuron-methyl, bensulfuron-methyl, pyrazosulfuron-ethyl, thiencsulfuron-methyl, halosulfuron-methyl, propyrisulfuron-methyl, metrisulfuron-methyl, rimsulfuron-methyl, flucarbazone-methyl, mesosulfuron-methyl, nicosulfuron-methyl, foramsulfuron-methyl, flumetsulam-methyl, triasulfuron-methyl, fluazincarbazide-methyl, penoxsulam-methyl, cloransulam-methyl, pyroxsulam-methyl, imazamox, imazethapyr, imazapyr, pyriminobac-methyl, florasulam, pyribenzoxim-methyl, propbensulfuron-methyl, imazethapyr-methyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, amidosulfuron, triasulfuron-methyl, tribenuron-methyl, iodosulfuron-methyl sodium, flazasulfuron-methyl, flucetosulfuron, metsulfuron-methyl, triflusulfuron-methyl, sulfosulfuron-methyl, pyrazosulfuron-methyl;
(5) ACCase inhibitors: clodinafop-propargyl, pinoxaden, clethodim, sethoxydim, quizalofop-p-ethyl, tralkoxydim, fluazifop-p-butyl, haloxyfop-methyl, diclofop-methyl, fenoxaprop-p-ethyl, cyhalofop-butyl, clethodim, metamifop, oxadiargyl;
(6) PPO inhibitors: oxyfluorfen, fomesafen, oxadiazon, oxadiargyl, sulfentrazone, pyraclonil, flumioxazin, pentoxazone, tiafenacil, saflufenacil, pyraflufen, carfentrazone-ethyl, butafenacil, trifluoromethoxyfen, triflumimoxazin, metribuzin, and ephedifenacil;
(7) PSII inhibitors: atrazine, prometryn, simetryn, terbuthylazine, terbutryn, ametryn, ipratron, fenfluryn, diquat, simazine, metribuzin, ethiprole, amicarbazone, metamitron, cyanazine, chlortoluron, isoproturon, diuron, fluometuron, linuron, buthiuron, sumuron, gluron, bromuron, glufosinate, pyridazinol, hexazinone, isoethazine, prodazine, bromacil, lenacil, triclopyr, thiuron, isoxauron, metoxuron, subtilon, trifluoxazine, cycloprozoximate, propanil, pyridate, desmetryn, bromoxynil octanoate, bromoxynil, ioxynil;
(8) microtubule assembly inhibitors: trifluralin, butralin, pendimethalin, dithiopyr, butyfluing, oryzalin, sulfluralin, flumetsulam, fenthizamide, natremit, chlorthal and butafosinate;
(9) microtubule combination inhibitors: diacyl urea;
(10) VLCFA inhibitors: acetochlor, butachlor, pretilachlor, metolachlor, mefenacet, s-metolachlor, flufenacet, napropamide, pyraflufen, anilofol, anilofos, xylfenamid, fentrazamide, triazolam, cafenstrole, mephos, metolachlor, propyzamide, dimethenamid, dimefluzamide, Fenoxasulfone;
(11) lipid synthesis (non-acetyl-coa carboxylase) inhibitors: prosulfocarb, molinate, prosulfocarb, furbengal, ethofumesate, triallate, dichlormate, dichlorvos, penflufen and penflufen;
(12) synthetic laserThe following elements: quinclorac, fluroxypyr, triclopyr, clopyralid, picloram, aminopyralid, dicamba, fluroxypyr, 2-methyl-4-chlorophenoxyacetic acid thioester, MCPB, 2-methyl-4-chlorophenoxypropionic acid, 2-methyl-4-sodium chlorophenoxyacetate, 2-methyl-4-chlorophenoxyacetic acid isooctyl ester, 2, 4-dichlorophenoxyacetic acid butyl ester, 2, 4-dichlorophenoxyacetic acid isooctyl ester, 2, 4-dichlorophenoxyacetic acid, chloroquinolinic acid, 2-methyl-4-chlorodimethylammonium salt, 2, 4-dichlorpropionic acid, 2, 4-dichlorbutanoic acid, benazolin, aminocyclopyrachlor, 2, 4-dichlorfenac acid,
Figure FDA0002677889100000021
(13) EPSPS inhibitors: glyphosate, phosphinothricin;
(14) a GS inhibitor: glufosinate, bialaphos, refined glufosinate;
(15) PSI inhibitor selected from paraquat, diquat;
(16) DHP inhibitors: asulam;
(17) cellulose synthesis inhibitors: triazinyl flufenacet, indexazine flufenacet;
(18) other herbicides: oxaziclomefone, cinmethylin, indanthrone, quinclomazone, cumyluron, tetflupyrlomet.
2. The weeding composition containing the N- (1,3, 4-oxadiazole-2-yl) aryl formamide compounds according to claim 1, wherein the weight ratio of A, B in the weeding composition is 1: 600-200: 1 and 1: 500-100: 1; preferably 1: 300-80: 1 and 1: 200-60: 1; more preferably 1:150 to 50:1 and 1:120 to 30: 1; further preferably 1: 100-20: 1 and 1: 80-15: 1; further preferred are 1:50 to 10:1, 1:30 to 5:1, 1:10 to 4:1 and 1:5 to 1: 1.
3.A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides according to claim 1 or 2, characterized in that the percentage by mass of a and B in the herbicidal composition is 1 to 95%, preferably 10 to 80% of the total.
4.A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides according to any one of claims 1 to 3, characterized in that conventional adjuvants are also included in the herbicidal composition.
5.A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides according to claim 4, characterized in that the conventional adjuvants include carriers or surfactants.
6. The herbicidal composition comprising an N- (1,3, 4-oxadiazol-2-yl) arylcarboxamide compound according to any one of claims 1 to 5, characterized in that the herbicidal composition further comprises at least one safener.
7.A herbicidal composition comprising N- (1,3, 4-oxadiazol-2-yl) arylcarboxamides according to claim 6, characterized in that the safener is selected from one or more of isoxadifen, cyprosulfamide, mefenpyr, cloquintocet, gibberellic acid, furilazole, mecamifen.
8. The herbicidal composition containing the N- (1,3, 4-oxadiazol-2-yl) arylcarboxamide compound according to any one of claims 1 to 7, characterized in that the specific formulation of the herbicidal composition is dispersible oil suspension, aqueous suspension, suspoemulsion, wettable powder, emulsifiable concentrate, water dispersible granules, aqueous emulsion or microemulsion.
9. Use of a herbicidal composition comprising an N- (1,3, 4-oxadiazol-2-yl) arylcarboxamide compound as claimed in any of claims 1 to 8 for controlling weeds.
10.A method for controlling unwanted plant growth, which comprises applying a herbicidal composition comprising an N- (1,3, 4-oxadiazol-2-yl) arylcarboxamide compound as claimed in any of claims 1 to 8 to a plant, to parts of a plant, to seeds of a plant or to the area where a plant is growing.
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