CA1221380A - Herbicidal 2-haloacetanilides - Google Patents

Herbicidal 2-haloacetanilides

Info

Publication number: CA1221380A
Authority: CA; Canada
Prior art keywords: compound; trifluoromethyl; methyl; chloroacetanilide; ethyl
Prior art date: 1980-03-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000373332A

Other languages

English (en)

French (fr)

Inventor

John P. Chupp

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Monsanto Co

Original Assignee

Monsanto Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-03-25

Filing date

1981-03-18

Publication date

1987-05-05

1981-03-18 Application filed by Monsanto Co filed Critical Monsanto Co

1987-05-05 Application granted granted Critical

1987-05-05 Publication of CA1221380A publication Critical patent/CA1221380A/en

Status Expired legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 64
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238000000034 method Methods 0.000 claims abstract description 41
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125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 12
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VJULAACBOCJUCR-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-ethyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(CC)C=CC=C1C(F)(F)F VJULAACBOCJUCR-UHFFFAOYSA-N 0.000 claims description 4
FTHUAISISRFQDD-UHFFFAOYSA-N 2-chloro-n-[2-ethyl-6-(trifluoromethyl)phenyl]-n-(propoxymethyl)acetamide Chemical compound CCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1C(F)(F)F FTHUAISISRFQDD-UHFFFAOYSA-N 0.000 claims description 4
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KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 claims 8
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AURQSJHVURCBRX-UHFFFAOYSA-N 2-chloro-n-[2-methyl-6-(trifluoromethyl)phenyl]-n-(propoxymethyl)acetamide Chemical compound CCCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F AURQSJHVURCBRX-UHFFFAOYSA-N 0.000 claims 3
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GYRTYUDXRCQENF-UHFFFAOYSA-N 6-chloro-2-n,4-n-diethyl-1,3,5-triazine-2,4-diamine;6-chloro-2-n,4-n-di(propan-2-yl)-1,3,5-triazine-2,4-diamine;6-chloro-4-n-ethyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1.CCNC1=NC(Cl)=NC(NC(C)C)=N1.CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 GYRTYUDXRCQENF-UHFFFAOYSA-N 0.000 description 1
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MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
IZJNBSCGGYVBGD-UHFFFAOYSA-N CNC(=O)N(C=1SC2=C(N1)C=CC=C2)C.ClC=2C=C(C=CC2Cl)NC(N(C)C)=O.CN(C(=O)NC2=CC(=C(C=C2)C)Cl)C.ClC2=CC=C(ON(C(N(C)C)=O)C1=CC=CC=C1)C=C2 Chemical compound CNC(=O)N(C=1SC2=C(N1)C=CC=C2)C.ClC=2C=C(C=CC2Cl)NC(N(C)C)=O.CN(C(=O)NC2=CC(=C(C=C2)C)Cl)C.ClC2=CC=C(ON(C(N(C)C)=O)C1=CC=CC=C1)C=C2 IZJNBSCGGYVBGD-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
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240000001579 Cirsium arvense Species 0.000 description 1
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235000012629 Mentha aquatica Nutrition 0.000 description 1
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ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
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229910052801 chlorine Inorganic materials 0.000 description 1
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CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
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238000005260 corrosion Methods 0.000 description 1
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230000001419 dependent effect Effects 0.000 description 1
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230000018109 developmental process Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
229940116901 diethyldithiocarbamate Drugs 0.000 description 1
LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000012010 growth Effects 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
239000003815 herbicide antidote Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
238000009533 lab test Methods 0.000 description 1
XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Chemical class 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
208000026435 phlegm Diseases 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
230000008654 plant damage Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
231100000817 safety factor Toxicity 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Plant Substances (AREA)

CA000373332A 1980-03-25 1981-03-18 Herbicidal 2-haloacetanilides Expired CA1221380A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13371880A	1980-03-25	1980-03-25
US133,718		1980-03-25

Publications (1)

Publication Number	Publication Date
CA1221380A true CA1221380A (en)	1987-05-05

Family

ID=22459986

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000373332A Expired CA1221380A (en)	1980-03-25	1981-03-18	Herbicidal 2-haloacetanilides

Country Status (40)

Country	Link
JP (1)	JPS56145260A (ro)
AR (1)	AR228451A1 (ro)
AT (1)	AT370279B (ro)
AU (1)	AU537092B2 (ro)
BE (1)	BE887997A (ro)
BG (1)	BG36192A3 (ro)
BR (1)	BR8101599A (ro)
CA (1)	CA1221380A (ro)
CH (1)	CH644586A5 (ro)
CS (1)	CS227326B2 (ro)
CY (1)	CY1278A (ro)
DD (1)	DD157295A5 (ro)
DE (1)	DE3110523C2 (ro)
DK (1)	DK157189C (ro)
EG (1)	EG15025A (ro)
FI (1)	FI73972C (ro)
FR (1)	FR2479204B1 (ro)
GB (1)	GB2072181B (ro)
GR (1)	GR66543B (ro)
HU (1)	HU189497B (ro)
IE (1)	IE51698B1 (ro)
IL (2)	IL62420A (ro)
IT (1)	IT1194040B (ro)
KE (1)	KE3480A (ro)
LU (1)	LU83232A1 (ro)
MA (1)	MA19103A1 (ro)
MW (1)	MW1181A1 (ro)
MX (1)	MX6765E (ro)
NL (1)	NL8101326A (ro)
NO (1)	NO151617C (ro)
NZ (1)	NZ196541A (ro)
OA (1)	OA06771A (ro)
PL (1)	PL125386B1 (ro)
PT (1)	PT72685B (ro)
RO (3)	RO85642B (ro)
SE (1)	SE462093B (ro)
SG (1)	SG86784G (ro)
TR (1)	TR20869A (ro)
ZA (2)	ZA828914B (ro)
ZW (1)	ZW6081A1 (ro)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA861043B (en) *	1985-02-13	1987-01-28	Monsanto Co	Novel acetanilides and their use in the regulation of the natural growth or development of turf grass

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH579348A5 (ro) *	1973-02-08	1976-09-15	Ciba Geigy Ag
CH585191A5 (en) *	1973-02-08	1977-02-28	Ciba Geigy Ag	N-substd halogen acetanilide herbicides - prepd. from N-substd anilines and chloracetic anhydride or chloracetyl chloride
PL103793B1 (pl) *	1976-03-19	1979-07-31	Monsanto Co	Srodek chwastobojczy
DE2803662A1 (de) *	1978-01-25	1979-07-26	Schering Ag	Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
US4258196A (en) *	1978-04-17	1981-03-24	Monsanto Company	Process for the production of tertiary 2-haloacetamides

1981
- 1981-03-18 TR TR20869A patent/TR20869A/xx unknown
- 1981-03-18 NL NL8101326A patent/NL8101326A/nl not_active Application Discontinuation
- 1981-03-18 PL PL1981230198A patent/PL125386B1/pl unknown
- 1981-03-18 ZA ZA828914A patent/ZA828914B/xx unknown
- 1981-03-18 CS CS811984A patent/CS227326B2/cs unknown
- 1981-03-18 CA CA000373332A patent/CA1221380A/en not_active Expired
- 1981-03-18 EG EG144/81A patent/EG15025A/xx active
- 1981-03-18 LU LU83232A patent/LU83232A1/fr unknown
- 1981-03-18 AR AR284653A patent/AR228451A1/es active
- 1981-03-18 BR BR8101599A patent/BR8101599A/pt unknown
- 1981-03-18 OA OA57357A patent/OA06771A/xx unknown
- 1981-03-18 FI FI810834A patent/FI73972C/fi not_active IP Right Cessation
- 1981-03-18 PT PT72685A patent/PT72685B/pt unknown
- 1981-03-18 AU AU68490/81A patent/AU537092B2/en not_active Ceased
- 1981-03-18 IT IT20413/81A patent/IT1194040B/it active
- 1981-03-18 DD DD81228415A patent/DD157295A5/de not_active IP Right Cessation
- 1981-03-18 JP JP3808481A patent/JPS56145260A/ja active Granted
- 1981-03-18 BG BG051267A patent/BG36192A3/xx unknown
- 1981-03-18 MX MX819355U patent/MX6765E/es unknown
- 1981-03-18 GB GB8108383A patent/GB2072181B/en not_active Expired
- 1981-03-18 ZA ZA00811808A patent/ZA811808B/xx unknown
- 1981-03-18 ZW ZW60/81A patent/ZW6081A1/xx unknown
- 1981-03-18 HU HU81693A patent/HU189497B/hu not_active IP Right Cessation
- 1981-03-18 MA MA19309A patent/MA19103A1/fr unknown
- 1981-03-18 NO NO810927A patent/NO151617C/no unknown
- 1981-03-18 SE SE8101736A patent/SE462093B/sv not_active IP Right Cessation
- 1981-03-18 GR GR64439A patent/GR66543B/el unknown
- 1981-03-18 DE DE3110523A patent/DE3110523C2/de not_active Expired
- 1981-03-18 MW MW11/81A patent/MW1181A1/xx unknown
- 1981-03-18 BE BE0/204164A patent/BE887997A/fr not_active IP Right Cessation
- 1981-03-18 FR FR8105442A patent/FR2479204B1/fr not_active Expired
- 1981-03-18 IL IL62420A patent/IL62420A/xx unknown
- 1981-03-18 IL IL62411A patent/IL62411A/xx unknown
- 1981-03-18 CY CY1278A patent/CY1278A/xx unknown
- 1981-03-18 AT AT0125681A patent/AT370279B/de not_active IP Right Cessation
- 1981-03-18 RO RO110027A patent/RO85642B/ro unknown
- 1981-03-18 DK DK120681A patent/DK157189C/da active
- 1981-03-18 RO RO81103729A patent/RO81727A/ro unknown
- 1981-03-18 CH CH185581A patent/CH644586A5/de not_active IP Right Cessation
- 1981-03-18 RO RO110026A patent/RO85641B/ro unknown
- 1981-03-18 IE IE596/81A patent/IE51698B1/en unknown
- 1981-03-18 NZ NZ196541A patent/NZ196541A/en unknown
1984
- 1984-11-29 KE KE3480A patent/KE3480A/xx unknown
- 1984-12-04 SG SG867/84A patent/SG86784G/en unknown

Also Published As

Publication number	Publication date
DK157189C (da)	1990-04-23
IE810596L (en)	1981-09-25
TR20869A (tr)	1982-11-18
GB2072181B (en)	1984-02-29
RO81727B (ro)	1983-05-30
ZA828914B (en)	1983-02-23
NO151617B (no)	1985-01-28
SE8101736L (sv)	1981-11-09
JPH0148260B2 (ro)	1989-10-18
AU537092B2 (en)	1984-06-07
RO85641A (ro)	1984-11-25
EG15025A (en)	1985-12-31
PT72685B (en)	1982-03-24
ZA811808B (en)	1983-02-23
GB2072181A (en)	1981-09-30
MA19103A1 (fr)	1981-10-01
NL8101326A (nl)	1981-10-16
RO85642A (ro)	1984-11-25
OA06771A (fr)	1982-06-30
FR2479204A1 (fr)	1981-10-02
MW1181A1 (en)	1983-02-09
JPS56145260A (en)	1981-11-11
DK157189B (da)	1989-11-20
CS227326B2 (en)	1984-04-16
AU6849081A (en)	1981-10-01
GR66543B (ro)	1981-03-26
DE3110523C2 (de)	1986-02-06
NO151617C (no)	1985-05-08
DE3110523A1 (de)	1982-01-14
IT8120413A0 (it)	1981-03-18
BR8101599A (pt)	1981-09-29
CH644586A5 (de)	1984-08-15
RO85641B (ro)	1984-11-30
AT370279B (de)	1983-03-10
IE51698B1 (en)	1987-02-18
PT72685A (en)	1981-04-01
DK120681A (da)	1981-09-26
AR228451A1 (es)	1983-03-15
DD157295A5 (de)	1982-11-03
KE3480A (en)	1985-01-04
NO810927L (no)	1981-09-28
MX6765E (es)	1986-06-27
IT1194040B (it)	1988-08-31
FI73972C (fi)	1987-12-10
CY1278A (en)	1985-07-05
FI73972B (fi)	1987-08-31
IL62411A (en)	1984-07-31
ZW6081A1 (en)	1981-08-05
IL62420A0 (en)	1981-05-20
SE462093B (sv)	1990-05-07
PL125386B1 (en)	1983-05-31
ATA125681A (de)	1982-08-15
IL62420A (en)	1985-06-30
SG86784G (en)	1985-06-07
NZ196541A (en)	1984-04-27
RO81727A (ro)	1983-06-01
FI810834L (fi)	1981-09-26
RO85642B (ro)	1984-11-30
BG36192A3 (en)	1984-09-14
BE887997A (fr)	1981-09-18
HU189497B (en)	1986-07-28
IL62411A0 (en)	1981-05-20
LU83232A1 (fr)	1981-10-30
FR2479204B1 (fr)	1985-08-16
PL230198A1 (ro)	1981-10-30

Publication	Publication Date	Title
US4261733A (en)	1981-04-14	Herbicidal compounds and method of preparation and use
KR850001330B1 (ko)	1985-09-19	3, 5-비스(트리플루오로메틸)페녹시 카르복실산과 그 유도체
US4465509A (en)	1984-08-14	Urea compounds and herbicidal compositions containing them
CA1221380A (en)	1987-05-05	Herbicidal 2-haloacetanilides
US4531966A (en)	1985-07-30	Herbicide compositions
EP0064353B1 (en)	1986-05-21	Use of 2,4-disubstituted-5-thiazolecarboxylic acids and derivatives for reducing injury to crop plants by acetamide herbicides
US4345938A (en)	1982-08-24	Herbicidal 2-haloacetanilides
US4761176A (en)	1988-08-02	Herbicidal 2-haloacetanilides
CA1221378A (en)	1987-05-05	Herbicidal 2-haloacetanilides
US4758263A (en)	1988-07-19	2-(2,5-difluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5 diones
CA1221379A (en)	1987-05-05	Herbicidal 2-haloacetanilides
US4731109A (en)	1988-03-15	Herbicidal 2-haloacetanilides
US4461642A (en)	1984-07-24	Herbicidal compositions and method
US4567299A (en)	1986-01-28	Herbicidal 2-haloacetanilides
CA1206165A (en)	1986-06-17	Herbicidal 2-haloacetanilides
US4606759A (en)	1986-08-19	Herbicidal 2-haloacetanilides
CA1196918A (en)	1985-11-19	3,5-bis(perfluoroalkyl)-2h-1,4-thiazine-2,6- dicarboxylates as herbicidal compounds
US4280834A (en)	1981-07-28	Novel diphenyl ether derivative and herbicidal composition containing the same as an active component
US4242123A (en)	1980-12-30	Herbicidal composition and method of use
GB2072177A (en)	1981-09-30	Herbicidal 2-Haloacetanilides
JPH0368865B2 (ro)	1991-10-30
GB2072183A (en)	1981-09-30	Herbicidal 2-Haloacetanilides
JPS6024095B2 (ja)	1985-06-11	アルキル置換シクロヘキセニルアセトアミド誘導体、その製法および除草剤
JPS6052121B2 (ja)	1985-11-18	シクロヘキセニルアセトアミド誘導体を含む除草剤
JPS6193150A (ja)	1986-05-12	シクロヘキセニルアセトアミド誘導体とその製法

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2004-05-05	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20040505