CA1248968A - Dichloroacetamides utilises comme antidotes dans les herbicides - Google Patents

Dichloroacetamides utilises comme antidotes dans les herbicides

Info

Publication number: CA1248968A
Authority: CA; Canada
Prior art keywords: herbicide; compound; propenyl; antidotal; compounds
Prior art date: 1979-12-26
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

CA000445884A

Other languages

English (en)

Inventor

Jay K. Rinehart

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.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology 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.)

1979-12-26

Filing date

1984-01-23

Publication date

1989-01-17

1979-12-26 Priority claimed from US06/106,434 external-priority patent/US4294764A/en

1980-11-19 Priority claimed from CA000364989A external-priority patent/CA1178286A/fr

1984-01-23 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1984-01-23 Priority to CA000445884A priority Critical patent/CA1248968A/fr

1989-01-17 Application granted granted Critical

1989-01-17 Publication of CA1248968A publication Critical patent/CA1248968A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 37
239000004009 herbicide Substances 0.000 title claims description 25
230000002605 anti-dotal effect Effects 0.000 title claims description 13
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 title description 2
230000002363 herbicidal effect Effects 0.000 claims abstract description 17
239000000203 mixture Substances 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 8
230000012010 growth Effects 0.000 claims description 12
241000196324 Embryophyta Species 0.000 claims description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 5
230000000885 phytotoxic effect Effects 0.000 claims description 4
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 description 3
239000002253 acid Substances 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 2
125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
-1 dioxane-2-ylmethyl Chemical group 0.000 abstract description 8
238000002360 preparation method Methods 0.000 abstract description 7
239000000729 antidote Substances 0.000 abstract description 2
229940075522 antidotes Drugs 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
235000002017 Zea mays subsp mays Nutrition 0.000 description 11
239000002689 soil Substances 0.000 description 11
240000008042 Zea mays Species 0.000 description 9
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
235000005822 corn Nutrition 0.000 description 9
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 8
230000006378 damage Effects 0.000 description 8
230000003054 hormonal effect Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
208000027418 Wounds and injury Diseases 0.000 description 5
208000014674 injury Diseases 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010348 incorporation Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004576 sand Substances 0.000 description 3
OISQRMLHYOLTJL-UHFFFAOYSA-N 2,2-dichloro-n-(1,3-dioxolan-2-ylmethyl)-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC1OCCO1 OISQRMLHYOLTJL-UHFFFAOYSA-N 0.000 description 2
DLCLIWPGKGWWND-UHFFFAOYSA-N 2,2-dichloro-n-(2,2-dimethoxyethyl)-n-prop-2-enylacetamide Chemical compound COC(OC)CN(CC=C)C(=O)C(Cl)Cl DLCLIWPGKGWWND-UHFFFAOYSA-N 0.000 description 2
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000482268 Zea mays subsp. mays Species 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
231100000208 phytotoxic Toxicity 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
IEBNVYBKZGBTFL-UHFFFAOYSA-N 2,2-dichloro-n-(2,2-dimethoxyethyl)-n-propan-2-ylacetamide Chemical compound COC(OC)CN(C(C)C)C(=O)C(Cl)Cl IEBNVYBKZGBTFL-UHFFFAOYSA-N 0.000 description 1
HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 1
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
BMWNTVIQLFDYTJ-UHFFFAOYSA-N 2-chloro-n-(2,3-dimethylphenyl)-n-(methoxymethyl)acetamide Chemical compound COCN(C(=O)CCl)C1=CC=CC(C)=C1C BMWNTVIQLFDYTJ-UHFFFAOYSA-N 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical compound CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004568 cement Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
238000005056 compaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
FUJWQGZPBSWGPX-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)propan-2-amine Chemical compound COC(OC)CNC(C)C FUJWQGZPBSWGPX-UHFFFAOYSA-N 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 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
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000445884A 1979-12-26 1984-01-23 Dichloroacetamides utilises comme antidotes dans les herbicides Expired CA1248968A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000445884A CA1248968A (fr)	1979-12-26	1984-01-23	Dichloroacetamides utilises comme antidotes dans les herbicides

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US10643379A	1979-12-26	1979-12-26
US06/106,434 US4294764A (en)	1979-12-26	1979-12-26	N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides
US106,433		1979-12-26
US106,434		1979-12-26
CA000364989A CA1178286A (fr)	1979-12-26	1980-11-19	Antidotes pour l'emploi avec les herbicides
CA000445884A CA1248968A (fr)	1979-12-26	1984-01-23	Dichloroacetamides utilises comme antidotes dans les herbicides

Publications (1)

Publication Number	Publication Date
CA1248968A true CA1248968A (fr)	1989-01-17

Family

ID=27166891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000445884A Expired CA1248968A (fr)	1979-12-26	1984-01-23	Dichloroacetamides utilises comme antidotes dans les herbicides

Country Status (1)

Country	Link
CA (1)	CA1248968A (fr)

1984
- 1984-01-23 CA CA000445884A patent/CA1248968A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-01-17	MKEX	Expiry

Publication	Publication Date	Title
US4294764A (en)	1981-10-13	N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides
CA1178286A (fr)	1984-11-20	Antidotes pour l'emploi avec les herbicides
US4443628A (en)	1984-04-17	Antidotal compounds for use with herbicides
PL97728B1 (pl)	1978-03-30	Srodek mikrobojczy i regulujacy wzrost roslin
RU2010525C1 (ru)	1994-04-15	Способ подавления роста сорняков
US4531970A (en)	1985-07-30	Antidotal compound and method
US4400197A (en)	1983-08-23	N-(Optionally substituted 1,3-dioxolan- or dioxan-2-ylmethyl)-N-alkyl, alkenyl, or alkynyl-2,2-dichloroacetamides
CA1138466A (fr)	1982-12-28	Composes heterocycliques comportant des substitutions 2-imino-1,3-dithio et 1,3- oxathio utilises comme antidotes des herbicides
US4623383A (en)	1986-11-18	Novel N- and optionally N-substituted (N-dichloro-acetyl)glycine amides with an antidote action
US4317310A (en)	1982-03-02	Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes
US4406686A (en)	1983-09-27	Haloalkylaminomethyldioxolane herbicide antidotes
JPH0161107B2 (fr)	1989-12-27
JPS63152367A (ja)	1988-06-24	３―パーフルオロアルキル―５―置換オキシイソオキサゾール誘導体およびそれを有効成分として含有する除草剤
KR860002107B1 (ko)	1986-11-26	α, α-디메틸페닐초산 아닐리드 유도체의 제조방법
EP0064353A1 (fr)	1982-11-10	La mise en oeuvre d'acides 5-thiazole carboxylique 2,4-disubstitués pour réduire les dégâts causés par les herbicides à base d'acétamide aux plantes de récolte
US4628101A (en)	1986-12-09	Compounds having a antidote activity for the protection of cultivations of agrarian interest from the action of nonselective herbicides
US4403444A (en)	1983-09-13	Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes
US4247322A (en)	1981-01-27	3-(m-Trifluoromethylphenyl)-5-halomethyl isoxazoles as safening agents
CA1205475A (fr)	1986-06-03	Derives de 1,3-thiazolidine
JPH0655705B2 (ja)	1994-07-27	アシルアミノバレロニトリル誘導体、その製造法およびそれらを含有する除草剤および農園芸用殺菌剤
US4512796A (en)	1985-04-23	Haloacetylaminomethyl dioxolane herbicide antidotes
US4454682A (en)	1984-06-19	Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes
US4098599A (en)	1978-07-04	Antidote compositions and method of use with herbicides
US4307238A (en)	1981-12-22	Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes
US4471571A (en)	1984-09-18	Substituted 2-imino-1,3-dithio and 1,3-oxathio heterocyclic compounds as herbicidal antidotes